An organic compound and an organic electroluminescent device using the same

Abstract

The present invention relates to the field of organic electroluminescence technology, and particularly relates to an organic compound, its application, and an organic electroluminescent device comprising the compound. Specifically, it relates to a novel thermally activated delayed fluorescence material having a structure represented by the following formula (1), wherein D 1 , D 2 , D 3 , D 4 , D 5 each independently represents a structure represented by formula (d1), formula (d2), formula (d3), formula (d4), formula (d5), or formula (d6), or is selected from a substituted or unsubstituted C3-C60 heteroaryl group. When the compound of the present invention is used as a light-emitting layer material in an OLED device, it has a higher photoluminescence quantum efficiency and a faster reverse intersystem crossing rate, and can exhibit excellent device efficiency and device lifetime. The present invention also protects an organic electroluminescent device using the above-mentioned organic compound.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and particularly to an organic compound, its application, and an organic electroluminescent device comprising the compound, and specifically to a thermally activated delayed fluorescence material. Background Art

[0002] Organic Light Emission Diodes (OLEDs) are devices with a sandwich-like structure, including positive and negative electrode film layers and an organic functional material layer sandwiched between the electrode film layers. When a voltage is applied to the electrodes of the OLED device, positive charges are injected from the positive electrode and negative charges are injected from the negative electrode. Under the action of an electric field, the positive and negative charges migrate and recombine in the organic layer to emit light. Due to the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility of OLED devices, they have attracted much attention in the fields of new display technology and new lighting technology. Currently, this technology has been widely applied to the display panels of new lighting fixtures, smartphones, tablet computers, etc., and will further expand to the application fields of large-size display products such as televisions. It is a new display technology with rapid development and high technical requirements.

[0003] With the continuous advancement of OLEDs in the two major fields of lighting and display, people have paid more attention to the research of their core materials. This is because an OLED device with good efficiency and long lifespan is usually the result of the optimization of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light-emitting host materials and light-emitting guests (dyes), etc.

[0004] In order to fabricate OLED light-emitting devices with lower driving voltage, better luminous efficiency, and longer device lifespan, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the OLED device structure and manufacturing process, but also to continuously research and innovate the optoelectronic functional materials in OLED devices to prepare functional materials with higher performance. Based on this, the OLED material industry has been committed to developing new organic electroluminescent materials to achieve low turn-on voltage, high luminous efficiency, and better service life of devices. Summary of the Invention

[0005] To solve the above technical problems, the present invention provides an organic compound that can be applied to the field of organic electroluminescence.

[0006] This organic compound of the present invention has the structure shown in the following formula (1):

[0007]

[0008] In formula (1), D 1 , D 2 , D 3 , D 4 , D 5 are the same or different, D 1 , D 2 , D 3 , D 4 , D 5 each independently selected from the structures represented by the following formula (d1), formula (d2), formula (d3), formula (d4), formula (d5) or formula (d6), or selected from substituted or unsubstituted C3-C60 heteroaryl; and D 1 , D 2 , D 3 , D 4 , D 5 at least one of them is selected from the structures represented by one of the formula (d1)-(d6), and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl;

[0009] When there are substituents on the above-mentioned heteroaryl, the substituents are selected from one or a combination of two of cyano, halogen, C1-C30 linear alkyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C2-C30 alkynyl, nitro, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl;

[0010]

[0011]

[0012] In formula (d1), each R is the same or different, and R is independently selected from one of hydrogen, deuterium, cyano, halogen, C1-C6 linear alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, and C1-C6 alkylsilyl, and not all Rs are hydrogen at the same time;In formula (d6), Y1 and Y2 each independently selected from O, S or Se, each R1 is the same or different, and R1 is independently selected from hydrogen, deuterium, cyano, halogen, C1-C30 linear alkyl, C1-C6 haloalkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl.

[0013] Preferably, in formula (d6), each R1 is independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, pivalyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, methoxy, phenyl, biphenyl, pyridyl, pyrimidinyl or triazinyl; more preferably, in formula (d6), each R1 is hydrogen.

[0014] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be elaborated one by one.

[0015] In this specification, the expression of Ca~Cb means that the group has a carbon atom number of a~b. Generally speaking, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0016] In this specification, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any bond-forming position on the ring structure.

[0017] In this specification, "independently of each other" means that when its subject has multiple ones, they may be the same or different from each other.

[0018] In the present invention, for the expression of chemical elements, unless otherwise specified, it usually includes the concept of its isotopes. For example, the expression of "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H), 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be elaborated further.

[0019] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, S, P, Si and Se, preferably selected from N, O, S.

[0020] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0021] In the present invention, unless otherwise specified, aryl and heteroaryl both include monocyclic and fused-ring cases.

[0022] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and fused-ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. The so-called monocyclic aryl group means that the molecule contains at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected by single bonds. Exemplarily, such as: phenyl group, biphenyl group, terphenyl group, etc. Specifically, the biphenyl group includes 2-biphenyl group, 3-biphenyl group, and 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl. The fused-ring aryl group means that the molecule contains at least two aromatic rings, and the aromatic rings are not independent of each other but are fused to each other by sharing two adjacent carbon atoms. Exemplarily, such as: naphthyl group, anthryl group, phenanthryl group, indenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, -yl group, tetraphenylenyl group and their derivative groups, etc. The naphthyl group includes 1-naphthyl group or 2-naphthyl group; the anthryl group is selected from 1-anthryl group, 2-anthryl group, and 9-anthryl group; the fluorenyl group is selected from 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, and 9-fluorenyl group; the pyrenyl group is selected from 1-pyrenyl group, 2-pyrenyl group, and 4-pyrenyl group; the tetraphenylenyl group is selected from 1-tetraphenylenyl group, 2-tetraphenylenyl group, and 9-tetraphenylenyl group. The derivative groups of fluorene are selected from 9,9-dimethylfluorenyl group, 9,9-diethylfluorenyl group, 9,9-dipropylfluorenyl group, 9,9-dibutylfluorenyl group, 9,9-dipentylfluorenyl group, 9,9-dihexylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-dinaphthylfluorenyl group, 9,9'-spirobifluorenyl group, and benzofluorenyl group.

[0023] The C3-C60 heteroaryl group mentioned in the present invention includes monocyclic heteroaryl groups and fused-ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and even more preferably C5-C12 heteroaryl groups. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl group, heteroaryl group, alkyl group, etc.), the heteroaryl group and other groups are independent of each other and are connected by single bonds. Examples of the monocyclic heteroaryl group include: furyl group, thienyl group, pyrrolyl group, pyridyl group, etc. The fused-ring heteroaryl group means that the molecule contains at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aromatic ring), and the two are not independent of each other but are fused to each other by sharing two adjacent atoms. Examples of the fused-ring heteroaryl group include: benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, acridinyl group, isobenzofuryl group, isobenzothienyl group, benzocarbazolyl group, azacarbazolyl group, phenothiazinyl group, phenazinyl group, 9-phenylcarbazolyl group, 9-naphthylcarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, etc.

[0024] In the present invention, the aryloxy group may be a monovalent group composed of the above-mentioned aryl group, heteroaryl group and oxygen.

[0025] In the present invention, the arylamino group represents a group formed by substituting one or two hydrogens on the amino group with aryl groups, wherein the connection site of the arylamino group may be connected to the aryl group in the arylamino group or to the N in the arylamino group. The exemplary carbon number and specific groups of the aryl group in the arylamino group are the same as those described above.

[0026] Examples of the C6-C30 arylamino group mentioned in the present invention include, for example: phenylamino group, methylphenylamino group, naphthylamino group, anthrylamino group, phenanthrylamino group, biphenylamino group, etc.

[0027] Examples of the C3-C30 heteroaryl amino group mentioned in the present invention include, for example: pyridylamino group, pyrimidinylamino group, dibenzofuranylamino group, etc.

[0028] In the present invention, the linear alkyl group, unless otherwise specified, includes a straight-chain alkyl group and a branched-chain alkyl group. Specifically, the substituted or unsubstituted C1-C30 linear alkyl group is preferably a substituted or unsubstituted C1-C16 linear alkyl group, and more preferably a substituted or unsubstituted C1-C10 linear alkyl group. Examples of the substituted or unsubstituted C1-C10 linear alkyl group include, for example: methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, n-pentyl group, sec-pentyl group, neopentyl group, n-hexyl group, neohexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, etc.

[0029] In the present invention, the cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group; wherein, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure; the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include, for example: cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group, etc.

[0030] It should be noted that in the present application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between various groups, rather than the effect of a single group.

[0031] More preferably, in the organic compound of the present invention, D 1 、D 2 、D 3 、D 4 、D 5 has a structure shown in one of the formulas (d1)-(d6), and at the same time D 1 、D 2 、D3 , D 4 , D 5 Among the four in, they are each independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, D 1 , D 2 , D 3 , D 4 , D 5 Two of them are the same or different, and the two are each independently selected from the structures shown in any one of formulas (d1)-(d4), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 The other three in are each independently selected from substituted or unsubstituted C3-C60 heteroaryl.

[0032] More preferably, in the organic compound of the present invention, D 2 , D 3 , D 4 One of them is selected from the structures shown in any one of formulas (d1)-(d6), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 The other four in are each independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, D 2 , D 3 , D 4 Two of them are the same or different, and the two are each independently selected from the structures shown in any one of formulas (d1)-(d6), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 The other three in are each independently selected from substituted or unsubstituted C3-C60 heteroaryl;

[0033] Preferably, D 2 or D 3 is selected from the structures shown in any one of formulas (d1)-(d6), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 The other four in are each independently selected from substituted or unsubstituted C3-C60 heteroaryl; More preferably, D 3 is selected from the structures shown in any one of formulas (d1)-(d6), and at the same time D 1 , D 2 , D 4 , D 5Independently selected from substituted or unsubstituted C3-C60 heteroaryl groups respectively.

[0034] Further preferably, in the organic compound of the present invention, the D 1 , D 2 , D 3 , D 4 , D 5 Among them, one is selected from the structure shown in formula (d1), and at the same time, D 1 , D 2 , D 3 , D 4 , D 5 Among them, four are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups; or, the D 1 , D 2 , D 3 , D 4 , D 5 Among them, two are independently selected from the structure shown in formula (d1), and at the same time, D 1 , D 2 , D 3 , D 4 , D 5 Among them, three are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups;

[0035] Preferably, D 2 or D 3 is selected from the structure shown in formula (d1), and at the same time, D 1 , D 2 , D 3 , D 4 , D 5 Among the other four are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups; more preferably, D 3 is selected from the structure shown in formula (d1), and at the same time, D 1 , D 2 , D 4 , D 5 Are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups;

[0036] Still more preferably, in formula (d1), R is independently selected from hydrogen, deuterium, cyano group, methyl group, ethyl group, propyl group, tert-butyl group, trifluoromethyl group, methoxy group or methylsilyl group, and each R is not hydrogen at the same time; further preferably, in formula (d1), one R is selected from hydrogen, deuterium, cyano group, methyl group, ethyl group, propyl group, tert-butyl group, trifluoromethyl group, methoxy group or methylsilyl group, and the remaining three Rs are hydrogen;

[0037] More preferably, the formula (d1) has the following structure:

[0038]

[0039] Most preferably, the formula (d1) has the structure shown below:

[0040]

[0041] Further preferably, in the organic compound of the present invention, the D 1 , D 2 , D 3 , D 4 , D 5 has one selected from the structures shown in one of the formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time, D 1 , D 2 , D 3 , D 4 , D 5 are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl groups; or, the D 1 , D 2 , D 3 , D 4 , D 5 has two respectively independently selected from the structures shown in one of the formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time, D 1 , D 2 , D 3 , D 4 , D 5 are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

[0042] Preferably, D 2 or D 3 is selected from the structures shown in one of the formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time, D 1 , D 2 , D 3 , D 4 , D 5 are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl groups; more preferably, D 3 is selected from the structures shown in one of the formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time, D 1 , D 2 , D 4 , D 5 are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

[0043] Further preferably, in the organic compound of the present invention, the D 1 , D 2 , D 3 , D4 , D 5 contains a structure selected from the formula (d6), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 among them, four are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl; or, said D 1 , D 2 , D 3 , D 4 , D 5 among them, two are respectively independently selected from the structures shown in formula (d6), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 among them, three are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl.

[0044] Preferably, D 2 or D 3 is selected from the structure shown in formula (d6), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 among the other four are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl; more preferably, D 3 is selected from the structure shown in formula (d6), and at the same time D 1 , D 2 , D 4 , D 5 are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl.

[0045] More preferably, in the organic compound of the present invention, when D 1 , D 2 , D 3 , D 4 , D 5 are respectively independently selected from substituted or unsubstituted C3-C60 heteroaryl, it is selected from one of the following substituted or unsubstituted structural formulas:

[0046]

[0047] When there are substituents on the above structural formula, the substituents are selected from one or a combination of two of deuterium, cyano, halogen, C1-C6 linear alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl;

[0048] More preferably, in the organic compound of the present invention, when D 1 、D 2 、D 3 、D 4 、D 5 are each independently selected from substituted or unsubstituted C3-C60 heteroaryl groups, they are selected from one of the following substituted or unsubstituted structural formulas:

[0049]

[0050] When there are substituents on the above structural formula, the substituents are selected from one of deuterium, C1-C6 linear alkyl groups, C3-C6 cycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups.

[0051] The structural design feature of the organic compound of the present invention is that in addition to containing a trifluoromethyl group as an electron acceptor, at least one benzonitrile, trifluoromethylphenyl, boroxine ring or xanthone group is introduced as a second acceptor. The presence of the trifluoromethyl group on the central benzene ring can ensure the matching of the LUMO orbital energy level of the molecule with the optical color of the material, ensure that the molecule has a small singlet-triplet energy difference, and at the same time, the trifluoromethyl group can be protected by the surrounding large conjugated steric hindrance groups, so that the LUMO orbital is distributed around the trifluoromethyl group as much as possible without interacting with the outside world to avoid the excited state quenching process. Benzonitrile, trifluoromethylphenyl, boroxine ring or xanthone group as the second acceptor, all of these six groups have at least one conjugated aromatic ring and strong electron-withdrawing ability, which can disperse the charge on the central benzene ring of the molecule through the conjugation effect, reduce the benzene ring charge density, and increase the BDE- of the C-N bond in the molecule, which is beneficial to improving the molecular stability, thereby achieving a longer device life. The selected heteroaryl electron donors and acceptors both have relatively high local triplet energy levels, which can achieve a small singlet-triplet energy difference. The combined use of multiple acceptor groups can form LUMO orbital energy levels with similar energies (including LUMO, LUMO+1, LUMO+2, etc.), and multiple donor groups in the molecule can also form HOMO orbital energy levels with similar energies (including HOMO, HOMO-1, HOMO-2, HOMO-3, etc.). These molecular orbitals with similar energies can generate excited state energy levels with similar energies during the excitation process. There is a second-order perturbation effect between these excited state energy levels, which enhances the excited state coupling and can simultaneously greatly increase the reverse intersystem crossing rate and radiative transition rate of the material, thereby achieving higher device efficiency. At the same time, the selected electron donors of the compounds of the present invention, such as carbazole derivatives, carboline derivatives, benzofurocarbazole or benzothiophenocarbazole and other heteroaryl groups, all have similar electron-donating abilities. Therefore, this type of compound of the present invention has predictable similar properties.

[0052] Furthermore, the compounds of the general formula (1) of the present invention may preferably include the following specific structural compounds, which are only representative:

[0053]

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[0055]

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[0132]

[0133] The present invention also protects the application of the compound represented by the above formula (1), and the application is as a functional material in an organic electronic device, and the organic electronic device includes: an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper, preferably an organic electroluminescent device.

[0134] The present invention also provides an organic electroluminescent device, including a substrate, including a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer contains the compound represented by the formula (1) of the present invention, or includes any one of the specific compounds A1-K140 of the present invention.

[0135] Specifically, an embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer formed in sequence on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains the compound represented by the formula (1) of the present invention, or includes any one of the specific compounds A1-K140 of the present invention.

[0136] The OLED device prepared by using the compound of the present invention has a low turn-on voltage, high luminous efficiency, and better service life. Detailed Embodiments

[0137] The following will take a plurality of synthesis examples as examples to detail the specific preparation method of the above new compound of the present invention, but the preparation method of the present invention is not limited to these synthesis examples. The synthesis method of the compound of the present invention will be briefly described below.

[0138] Synthesis Examples

[0139] Synthesis of Intermediate 1:

[0140]

[0141] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), 4-cyanophenylboronic acid (5.44 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain white solid intermediate 1, weighing 7.6 g, with a yield of 71%.

[0142] Synthesis of Intermediate 2:

[0143]

[0144] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), 4-trifluoromethylphenylboronic acid (5.44 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain white solid intermediate 2, weighing 9.9 g, with a yield of 81%.

[0145] Synthesis of Intermediate 3:

[0146]

[0147] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), (2,12-Di-tert-butyl-5,9-dioxa-13b-borata-anthra[3,2,1-de]anthracen-7-yl)boronic acid (15.78 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain white solid intermediate 3, weighing 14.9 g, with a yield of 74%.

[0148] Synthesis of Intermediate 4:

[0149]

[0150] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), (3,11-Di-tert-butyl-5,9-dioxa-13b-borataanthra[3,2,1-de]anthracen-7-yl)boronic acid (18.46 g, 43.31 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added, and the mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 4, weighing 14.9 g, with a yield of 74%.

[0151] Synthesis of Intermediate 5:

[0152]

[0153] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), xanthone-2-boronic acid (8.89 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added, and the mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 5, weighing 10.9 g, with a yield of 78%.

[0154] Synthesis of Intermediate 6:

[0155]

[0156] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), xanthone-1-boronic acid (8.89 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added, and the mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 5, weighing 9.4 g, with a yield of 68%.

[0157] Synthesis of Intermediate 7:

[0158]

[0159] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), xanthone-3-boronic acid (8.89 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 5, weighing 9.9 g, with a yield of 71%.

[0160] Synthesis of intermediate 8:

[0161]

[0162] 1-Bromo-2,3,4,6-tetrafluoro-5-trifluoromethylbenzene (10 g, 33.67 mmol), xanthone-4-boronic acid (8.89 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.31 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 5, weighing 10.5 g, with a yield of 76%.

[0163] Synthesis Example A1:

[0164]

[0165] Weigh intermediate 1 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry, and purify by column chromatography to obtain compound A1, a yellow solid, with a yield of 93%. Mass spectrometry: m / z 907.29, elemental analysis experimental values: C, 82.01; H, 4.00; F, 6.28; N, 7.71.

[0166] Synthesis Example A2:

[0167] The synthesis method is similar to A1, a yellow solid, with a yield of 89%. Mass spectrometry: m / z 963.35, elemental analysis experimental values: C, 82.22; H, 4.60; F, 5.91; N, 7.26.

[0168] Synthesis Example A3:

[0169] The synthesis method is similar to A1, a yellow solid, with a yield of 83%. Mass spectrometry: m / z 1019.42, elemental analysis experimental values: C, 82.41; H, 5.14; F, 5.59; N, 6.86.

[0170] Synthesis Example A4:

[0171] The synthesis method is similar to that of A1, a yellow solid with a yield of 80%. Mass spectrum: m / z 1075.48, experimental values of elemental analysis: C, 82.58; H, 5.62; F, 5.30; N, 6.51.

[0172] Synthesis Example A5:

[0173] The synthesis method is similar to that of A1, a yellow solid with a yield of 83%. Mass spectrum: m / z 1243.67, experimental values of elemental analysis: C, 82.99; H, 6.80; F, 4.58; N, 5.63.

[0174] Synthesis Example A6:

[0175] The synthesis method is similar to that of A1, a yellow solid with a yield of 89%. Mass spectrum: m / z 1131.54, experimental values of elemental analysis: C, 82.73; H, 6.05; F, 5.03; N, 6.18.

[0176] Synthesis Example A7:

[0177] The synthesis method is similar to that of A1, a yellow solid with a yield of 86%. Mass spectrum: m / z 1355.79, experimental values of elemental analysis: C, 83.21; H, 7.43; F, 4.20; N, 5.16.

[0178] Synthesis Example A8:

[0179] The synthesis method is similar to that of A1, a yellow solid with a yield of 83%. Mass spectrum: m / z 1195.45, experimental values of elemental analysis: C, 74.27; H, 5.73; F, 4.76; N, 5.85; Si, 9.39.

[0180] Synthesis Example A9:

[0181] The synthesis method is similar to that of A1, a yellow solid with a yield of 76%. Mass spectrum: m / z 1483.61, experimental values of elemental analysis: C, 69.54; H, 6.79; F, 3.84; N, 4.71; Si, 15.13.

[0182] Synthesis Example A10:

[0183] The synthesis method is similar to that of A1, a yellow solid with a yield of 65%. Mass spectrum: m / z 1007.27, experimental values of elemental analysis: C, 78.64; H, 3.20; F, 5.65; N, 12.51.

[0184] Synthesis Example A11:

[0185] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1107.25. Experimental values of elemental analysis: C, 75.88; H, 2.55; F, 5.14; N, 16.43.

[0186] Synthesis Example A12:

[0187] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1195.45. Experimental values of elemental analysis: C, 85.20; H, 4.32; F, 4.70; N, 5.78.

[0188] Synthesis Example A13:

[0189] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 53%. Mass spectrum: m / z 1515.54. Experimental values of elemental analysis: C, 87.11; H, 4.52; F, 3.76; N, 4.62.

[0190] Synthesis Example A14:

[0191] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1179.24. Experimental values of elemental analysis: C, 67.18; H, 2.73; F, 24.15; N, 5.94.

[0192] Synthesis Example A15:

[0193] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 81%. Mass spectrum: m / z 1451.19. Experimental values of elemental analysis: C, 57.90; H, 1.94; F, 35.33; N, 4.82.

[0194] Synthesis Example A16:

[0195] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1379.61. Experimental values of elemental analysis: C, 85.25; H, 5.55; F, 4.13; N, 5.07.

[0196] Synthesis Example A17:

[0197] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1851.92. Experimental values of elemental analysis: C, 86.84; H, 6.31; F, 3.08; N, 3.78.

[0198] Synthesis Example A18:

[0199] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 85%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0200] Synthesis Example A19:

[0201] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 86%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0202] Synthesis Example A20:

[0203] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0204] Synthesis Example A21:

[0205] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0206] Synthesis Example A35:

[0207] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1267.33. Experimental values of elemental analysis: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0208] Synthesis Example A36:

[0209] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1267.33. Experimental values of elemental analysis: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0210] Synthesis Example A37:

[0211] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 56%. Mass spectrometry: m / z 1267.33. Experimental values of elemental analysis: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0212] Synthesis Example A38:

[0213] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 40%. Mass spectrum: m / z 1267.33. Experimental values of elemental analysis: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0214] Synthesis Example A39:

[0215] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1225.34. Experimental values of elemental analysis: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0216] Synthesis Example A40:

[0217] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 60%. Mass spectrum: m / z 1225.34. Experimental values of elemental analysis: C, 81.44; H, 3.50; F, 4.49; N, 5.52; O, 5.05.

[0218] Synthesis Example A41:

[0219] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1331.24. Experimental values of elemental analysis: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0220] Synthesis Example A42:

[0221] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1331.24. Experimental values of elemental analysis: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0222] Synthesis Example A43:

[0223] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1331.24. Experimental values of elemental analysis: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0224] Synthesis Example A44:

[0225] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1331.24. Experimental values of elemental analysis: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0226] Synthesis Example A45:

[0227] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 68%. Mass spectrometry: m / z 1331.24. Experimental values of elemental analysis: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0228] Synthesis Example A46:

[0229] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 64%. Mass spectrometry: m / z 1331.24. Experimental values of elemental analysis: C, 77.52; H, 3.33; F, 4.28; N, 5.26; S, 9.62.

[0230] Synthesis Example A47:

[0231]

[0232] Weigh intermediate 2 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A47 by column chromatography. It is a yellow solid with a yield of 93%. Mass spectrometry: m / z 950.28. Experimental values of elemental analysis: C, 78.31; H, 3.82; F, 11.99; N, 5.89.

[0233] Synthesis Example A52:

[0234] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 89%. Mass spectrometry: m / z 1174.53. Experimental values of elemental analysis: C, 79.70; H, 5.83; F, 9.70; N, 4.77

[0235] Synthesis Example A53:

[0236] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1398.79. Experimental values of elemental analysis: C, 80.65; H, 7.20; F, 8.14; N, 4.00

[0237] Synthesis Example A54:

[0238] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 1238.44. Experimental values of elemental analysis: C, 71.69; H, 5.53; F, 9.19; N, 4.52; Si, 9.06

[0239] Synthesis Example A55:

[0240] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1526.60. Experimental values of elemental analysis: C, 67.58; H, 6.59; F, 7.46; N, 3.67; Si, 14.70.

[0241] Synthesis Example A58:

[0242] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 89%. Mass spectrum: m / z 1254.41. Experimental values of elemental analysis: C, 82.28; H, 4.18; F, 9.08; N, 4.46.

[0243] Synthesis Example A81:

[0244] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 86%. Mass spectrum: m / z 1310.33. Experimental values of elemental analysis: C, 78.77; H, 3.38; F, 8.69; N, 4.27; O, 4.88.

[0245] Synthesis Example A82:

[0246] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1310.33. Experimental values of elemental analysis: C, 78.77; H, 3.38; F, 8.69; N, 4.27; O, 4.88.

[0247] Synthesis Example A83:

[0248] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 76%. Mass spectrum: m / z 1310.33. Experimental values of elemental analysis: C, 78.77; H, 3.38; F, 8.69; N, 4.27; O, 4.88.

[0249] Synthesis Example A84:

[0250] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 65%. Mass spectrum: m / z 1310.33. Experimental values of elemental analysis: C, 78.77; H, 3.38; F, 8.69; N, 4.27; O, 4.88.

[0251] Synthesis Example A85:

[0252] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1310.33. Experimental values of elemental analysis: C, 78.77; H, 3.38; F, 8.69; N, 4.27; O, 4.88.

[0253] Synthesis Example A86:

[0254] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1310.33. Experimental values of elemental analysis: C, 78.77; H, 3.38; F, 8.69; N, 4.27; O, 4.88.

[0255] Synthesis Example A87:

[0256] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 53%. Mass spectrum: m / z 1374.24. Experimental values of elemental analysis: C, 75.09; H, 3.22; F, 8.29; N, 4.07; S, 9.32.

[0257] Synthesis Example A88:

[0258] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1374.24. Experimental values of elemental analysis: C, 75.09; H, 3.22; F, 8.29; N, 4.07; S, 9.32.

[0259] Synthesis Example A89:

[0260] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 81%. Mass spectrum: m / z 1374.24. Experimental values of elemental analysis: C, 75.09; H, 3.22; F, 8.29; N, 4.07; S, 9.32.

[0261] Synthesis Example A90:

[0262] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1374.24. Experimental values of elemental analysis: C, 75.09; H, 3.22; F, 8.29; N, 4.07; S, 9.32.

[0263] Synthesis Example A91:

[0264] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1374.24. Experimental values of elemental analysis: C, 75.09; H, 3.22; F, 8.29; N, 4.07; S, 9.32.

[0265] Synthesis Example A92:

[0266] The synthesis method is similar to that of A47. It is a yellow solid with a yield of 85%. Mass spectrum: m / z 1374.24. Experimental values of elemental analysis: C, 75.09; H, 3.22; F, 8.29; N, 4.07; S, 9.32.

[0267] Synthesis Example A93:

[0268]

[0269] Weigh intermediate 3 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A93 by column chromatography. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1186.46, elemental analysis experimental values: C, 81.95; H, 4.92; B, 0.91; F, 4.80; N, 4.72; O, 2.70.

[0270] Synthesis Example A98:

[0271] The synthesis method is similar to that of A93. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1410.71, elemental analysis experimental values: C, 82.53; H, 6.43; B, 0.77; F, 4.04; N, 3.97; O, 2.27.

[0272] Synthesis Example A99:

[0273] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1634.96, elemental analysis experimental values: C, 82.96; H, 7.52; B, 0.66; F, 3.48; N, 3.42; O, 1.96.

[0274] Synthesis Example A100:

[0275] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1474.62, elemental analysis experimental values: C, 75.68; H, 6.15; B, 0.73; F, 3.86; N, 3.80; O, 2.17; Si, 7.61.

[0276] Synthesis Example A101:

[0277] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1762.78, elemental analysis experimental values: C, 71.47; H, 6.97; B, 0.61; F, 3.23; N, 3.18; O, 1.81; Si, 12.73.

[0278] Synthesis Example A104:

[0279] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 56%. Mass spectrum: m / z 1490.59, elemental analysis experimental values: C, 84.55; H, 5.00; B, 0.72; F, 3.82; N, 3.76; O, 2.15.

[0280] Synthesis Example A127:

[0281] The synthesis method is similar to that of A1, a yellow solid with a yield of 40%. Mass spectrum: m / z 1546.50, experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0282] Synthesis Example A128:

[0283] The synthesis method is similar to that of A1, a yellow solid with a yield of 80%. Mass spectrum: m / z 1546.50, experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0284] Synthesis Example A129:

[0285] The synthesis method is similar to that of A1, a yellow solid with a yield of 60%. Mass spectrum: m / z 1546.50, experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0286] Synthesis Example A130:

[0287] The synthesis method is similar to that of A1, a yellow solid with a yield of 70%. Mass spectrum: m / z 1546.50, experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0288] Synthesis Example A131:

[0289] The synthesis method is similar to that of A1, a yellow solid with a yield of 59%. Mass spectrum: m / z 1546.50, experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0290] Synthesis Example A132:

[0291] The synthesis method is similar to that of A1, a yellow solid with a yield of 55%. Mass spectrum: m / z 1546.50, experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0292] Synthesis Example A133:

[0293] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0294] Synthesis Example A134:

[0295] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 68%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0296] Synthesis Example A135:

[0297] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 64%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0298] Synthesis Example A136:

[0299] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0300] Synthesis Example A137:

[0301] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 68%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0302] Synthesis Example A138:

[0303] The synthesis method is similar to that of A1. It is a yellow solid with a yield of 64%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0304] Synthesis Example A139:

[0305]

[0306] Weigh intermediate 4 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A139 by column chromatography, a yellow solid with a yield of 63%. Mass spectrum: m / z 1186.46, experimental values of elemental analysis: C, 81.95; H, 4.92; B, 0.91; F, 4.80; N, 4.72; O, 2.70.

[0307] Synthesis Example A144:

[0308] The synthesis method is similar to that of A139, a yellow solid with a yield of 70%. Mass spectrum: m / z 1410.71, experimental values of elemental analysis: C, 82.53; H, 6.43; B, 0.77; F, 4.04; N, 3.97; O, 2.27.

[0309] Synthesis Example A145:

[0310] The synthesis method is similar to that of A139, a yellow solid with a yield of 55%. Mass spectrum: m / z 1634.96, experimental values of elemental analysis: C, 82.96; H, 7.52; B, 0.66; F, 3.48; N, 3.42; O, 1.96.

[0311] Synthesis Example A146:

[0312] The synthesis method is similar to that of A139, a yellow solid with a yield of 83%. Mass spectrum: m / z 1474.62, experimental values of elemental analysis: C, 75.68; H, 6.15; B, 0.73; F, 3.86; N, 3.80; O, 2.17; Si, 7.61.

[0313] Synthesis Example A147:

[0314] The synthesis method is similar to that of A139, a yellow solid with a yield of 72%. Mass spectrum: m / z 1762.78, experimental values of elemental analysis: C, 71.47; H, 6.97; B, 0.61; F, 3.23; N, 3.18; O, 1.81; Si, 12.73.

[0315] Synthesis Example A150:

[0316] The synthesis method is similar to that of A139, a yellow solid with a yield of 56%. Mass spectrum: m / z 1490.59, experimental values of elemental analysis: C, 84.55; H, 5.00; B, 0.72; F, 3.82; N, 3.76; O, 2.15.

[0317] Synthesis Example A173:

[0318] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 40%. Mass spectrum: m / z 1546.50. Experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0319] Synthesis Example A174:

[0320] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1546.50. Experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0321] Synthesis Example A175:

[0322] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 60%. Mass spectrum: m / z 1546.50. Experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0323] Synthesis Example A176:

[0324] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1546.50. Experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0325] Synthesis Example A177:

[0326] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1546.50. Experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0327] Synthesis Example A178:

[0328] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1546.50. Experimental values of elemental analysis: C, 81.50; H, 4.30; B, 0.70; F, 3.68; N, 3.62; O, 6.20.

[0329] Synthesis Example A179:

[0330] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0331] Synthesis Example A180:

[0332] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0333] Synthesis Example A181:

[0334] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 88%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0335] Synthesis Example A182:

[0336] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 87%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0337] Synthesis Example A183:

[0338] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 86%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0339] Synthesis Example A184:

[0340] The synthesis method is similar to that of A139. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1610.41. Experimental values of elemental analysis: C, 78.25; H, 4.13; B, 0.67; F, 3.54; N, 3.48; O, 1.99; S, 7.96.

[0341] Synthesis Example A185:

[0342]

[0343] Weigh intermediate 5 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A185 by column chromatography, which is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0344] Synthesis Example A190:

[0345] The synthesis method is similar to that of A185, which is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1224.55, elemental analysis experimental values: C, 82.33; H, 5.84; F, 4.65; N, 4.57; O, 2.61.

[0346] Synthesis Example A191:

[0347] The synthesis method is similar to that of A185, which is a yellow solid with a yield of 91%. Mass spectrometry: m / z 1448.80, elemental analysis experimental values: C, 82.84; H, 7.16; F, 3.93; N, 3.86; O, 2.21.

[0348] Synthesis Example A192:

[0349] The synthesis method is similar to that of A185, which is a yellow solid with a yield of 82%. Mass spectrometry: m / z 1288.46, elemental analysis experimental values: C, 74.50; H, 5.55; F, 4.42; N, 4.34; O, 2.48; Si, 8.71.

[0350] Synthesis Example A193:

[0351] The synthesis method is similar to that of A185, which is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1576.62, elemental analysis experimental values: C, 70.00; H, 6.58; F, 3.61; N, 3.55; O, 2.03; Si, 14.23.

[0352] Synthesis Example A196:

[0353] The synthesis method is similar to that of A185, which is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1304.43, elemental analysis experimental values: C, 84.64; H, 4.25; F, 4.37; N, 4.29; O, 2.45.

[0354] Synthesis Example A231:

[0355]

[0356] Weigh intermediate 6 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A231 by column chromatography. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0357] Synthesis Example A236:

[0358] The synthesis method is similar to that of A231. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1224.55, elemental analysis experimental values: C, 82.33; H, 5.84; F, 4.65; N, 4.57; O, 2.61.

[0359] Synthesis Example A237:

[0360] The synthesis method is similar to that of A231. It is a yellow solid with a yield of 81%. Mass spectrometry: m / z 1448.80, elemental analysis experimental values: C, 82.84; H, 7.16; F, 3.93; N, 3.86; O, 2.21.

[0361] Synthesis Example A238:

[0362] The synthesis method is similar to that of A231. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1288.46, elemental analysis experimental values: C, 74.50; H, 5.55; F, 4.42; N, 4.34; O, 2.48; Si, 8.71.

[0363] Synthesis Example A239:

[0364] The synthesis method is similar to that of A231. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1576.62, elemental analysis experimental values: C, 70.00; H, 6.58; F, 3.61; N, 3.55; O, 2.03; Si, 14.23.

[0365] Synthesis Example A242:

[0366] The synthesis method is similar to that of A231. It is a yellow solid with a yield of 82%. Mass spectrometry: m / z 1304.43, elemental analysis experimental values: C, 84.64; H, 4.25; F, 4.37; N, 4.29; O, 2.45.

[0367] Synthesis Example A277:

[0368]

[0369] Weigh intermediate 7 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A277 by column chromatography, which is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0370] Synthesis Example A282:

[0371] The synthesis method is similar to that of A231, which is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1224.55, elemental analysis experimental values: C, 82.33; H, 5.84; F, 4.65; N, 4.57; O, 2.61.

[0372] Synthesis Example A283:

[0373] The synthesis method is similar to that of A231, which is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1448.80, elemental analysis experimental values: C, 82.84; H, 7.16; F, 3.93; N, 3.86; O, 2.21.

[0374] Synthesis Example A284:

[0375] The synthesis method is similar to that of A231, which is a yellow solid with a yield of 65%. Mass spectrometry: m / z 1288.46, elemental analysis experimental values: C, 74.50; H, 5.55; F, 4.42; N, 4.34; O, 2.48; Si, 8.71.

[0376] Synthesis Example A285:

[0377] The synthesis method is similar to that of A231, which is a yellow solid with a yield of 54%. Mass spectrometry: m / z 1576.62, elemental analysis experimental values: C, 70.00; H, 6.58; F, 3.61; N, 3.55; O, 2.03; Si, 14.23.

[0378] Synthesis Example A288:

[0379] The synthesis method is similar to that of A231, which is a yellow solid with a yield of 74%. Mass spectrometry: m / z 1304.43, elemental analysis experimental values: C, 84.64; H, 4.25; F, 4.37; N, 4.29; O, 2.45.

[0380] Synthesis Example A323:

[0381]

[0382] Weigh intermediate 8 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound A323 by column chromatography. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1000.30. Experimental values of elemental analysis: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0383] Synthesis Example A328:

[0384] The synthesis method is similar to that of A323. It is a yellow solid with a yield of 84%. Mass spectrum: m / z 1224.55. Experimental values of elemental analysis: C, 82.33; H, 5.84; F, 4.65; N, 4.57; O, 2.61.

[0385] Synthesis Example A329:

[0386] The synthesis method is similar to that of A323. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1448.80. Experimental values of elemental analysis: C, 82.84; H, 7.16; F, 3.93; N, 3.86; O, 2.21.

[0387] Synthesis Example A330:

[0388] The synthesis method is similar to that of A323. It is a yellow solid with a yield of 64%. Mass spectrum: m / z 1288.46. Experimental values of elemental analysis: C, 74.50; H, 5.55; F, 4.42; N, 4.34; O, 2.48; Si, 8.71.

[0389] Synthesis Example A331:

[0390] The synthesis method is similar to that of A323. It is a yellow solid with a yield of 69%. Yield 54%. Mass spectrum: m / z 1576.62. Experimental values of elemental analysis: C, 70.00; H,

[0391] 6.58; F, 3.61; N, 3.55; O, 2.03; Si, 14.23.

[0392] Synthesis Example A334:

[0393] The synthesis method is similar to that of A323. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1304.43. Experimental values of elemental analysis: C, 84.64; H, 4.25; F, 4.37; N, 4.29; O, 2.45.

[0394] Synthesis of Intermediate 9:

[0395]

[0396] 2-Bromo-3,4,5,6-tetrafluorobenzonitrile (10 g, 39.37 mmol) and 4-cyanophenylboronic acid (6.36 g, 43.31 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (2.27 g, 1.97 mmol) and 20 mL of aqueous potassium carbonate solution (10.88 g, 78.57 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, liquid separation, extraction, and drying were carried out. Column chromatography (petroleum ether:dichloromethane = 3:1) gave white solid Intermediate 9, weighing 8.9 g, with a yield of 82%.

[0397] Synthesis of Intermediates 10 - 16:

[0398]

[0399] The synthesis method was similar to that of Intermediate 9. Intermediates 10 - 16 were all white solids, and their yields were 75%, 66%, 75%, 81%, 65%, 76%, and 69% respectively.

[0400] Synthesis Example B1:

[0401] Weigh Intermediate 9 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and perform column chromatography to obtain Compound B1, a yellow solid, with a yield of 93%. Mass spectrometry: m / z 907.29, elemental analysis experimental values: C, 82.01; H, 4.00; F, 6.28; N, 7.71.

[0402] Synthesis Example B2:

[0403] The synthesis method was similar to that of B1, a yellow solid, with a yield of 89%. Mass spectrometry: m / z 963.35, elemental analysis experimental values: C, 82.22; H, 4.60; F, 5.91; N, 7.26.

[0404] Synthesis Example B3:

[0405] The synthesis method was similar to that of B1, a yellow solid, with a yield of 83%. Mass spectrometry: m / z 1019.42, elemental analysis experimental values: C, 82.41; H, 5.14; F, 5.59; N, 6.86.

[0406] Synthesis Example B4:

[0407] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1075.48. Experimental values of elemental analysis: C, 82.58; H, 5.62; F, 5.30; N, 6.51.

[0408] Synthesis Example B5:

[0409] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1243.67. Experimental values of elemental analysis: C, 82.99; H, 6.80; F, 4.58; N, 5.63.

[0410] Synthesis Example B6:

[0411] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 89%. Mass spectrum: m / z 1131.54. Experimental values of elemental analysis: C, 82.73; H, 6.05; F, 5.03; N, 6.18.

[0412] Synthesis Example B7:

[0413] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 86%. Mass spectrum: m / z 1355.79. Experimental values of elemental analysis: C, 83.21; H, 7.43; F, 4.20; N, 5.16.

[0414] Synthesis Example B8:

[0415] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1195.45. Experimental values of elemental analysis: C, 74.27; H, 5.73; F, 4.76; N, 5.85; Si, 9.39.

[0416] Synthesis Example B9:

[0417] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 76%. Mass spectrum: m / z 1483.61. Experimental values of elemental analysis: C, 69.54; H, 6.79; F, 3.84; N, 4.71; Si, 15.13.

[0418] Synthesis Example B10:

[0419] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 65%. Mass spectrum: m / z 1007.27. Experimental values of elemental analysis: C, 78.64; H, 3.20; F, 5.65; N, 12.51.

[0420] Synthesis Example B11:

[0421] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1107.25. Experimental values of elemental analysis: C, 75.88; H, 2.55; F, 5.14; N, 16.43.

[0422] Synthesis Example B12:

[0423] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1211.42. Experimental values of elemental analysis: C, 85.20; H, 4.32; F, 4.70; N, 5.78.

[0424] Synthesis Example B13:

[0425] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 53%. Mass spectrum: m / z 1515.54. Experimental values of elemental analysis: C, 87.11; H, 4.52; F, 3.76; N, 4.62.

[0426] Synthesis Example B14:

[0427] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1179.24. Experimental values of elemental analysis: C, 67.18; H, 2.73; F, 24.15; N, 5.94.

[0428] Synthesis Example B15:

[0429] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 81%. Mass spectrum: m / z 1451.19. Experimental values of elemental analysis: C, 57.90; H, 1.94; F, 35.33; N, 4.82.

[0430] Synthesis Example B16:

[0431] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1379.61. Experimental values of elemental analysis: C, 85.25; H, 5.55; F, 4.13; N, 5.07.

[0432] Synthesis Example B17:

[0433] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1851.92. Experimental values of elemental analysis: C, 86.84; H, 6.31; F, 3.08; N, 3.78.

[0434] Synthesis Example B18:

[0435] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 85%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0436] Synthesis Example B19:

[0437] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 86%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0438] Synthesis Example B20:

[0439] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0440] Synthesis Example B21:

[0441] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 911.27. Experimental values of elemental analysis: C, 76.39; H, 3.54; F, 6.25; N, 13.82.

[0442] Synthesis Example B22:

[0443] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 971.27. Experimental values of elemental analysis: C, 76.61; H, 3.73; F, 5.86; N, 7.21; O, 6.58.

[0444] Synthesis Example B23:

[0445] The synthesis method is similar to that of B1. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1035.18. Experimental values of elemental analysis: C, 71.86; H, 3.50; F, 5.50; N, 6.76; S, 12.38.

[0446] Synthesis Example B24:

[0447] Weigh intermediate 10 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound B24 by column chromatography. It is a yellow solid with a yield of 93%. Mass spectrometry: m / z 950.28. Experimental values of elemental analysis: C, 78.31; H, 3.82; F, 11.99; N, 5.89.

[0448] Synthesis Example B29:

[0449] The synthesis method was similar to that of B24, a yellow solid with a yield of 89%. Mass spectrometry: m / z 1174.53, experimental values of elemental analysis: C, 79.70; H, 5.83; F, 9.70; N, 4.77.

[0450] Synthesis Example B30:

[0451] The synthesis method was similar to that of B24, a yellow solid with a yield of 83%. Mass spectrometry: m / z 1398.79, experimental values of elemental analysis: C, 80.65; H, 7.20; F, 8.14; N, 4.00.

[0452] Synthesis Example B31:

[0453] The synthesis method was similar to that of B24, a yellow solid with a yield of 80%. Mass spectrometry: m / z 1238.44, experimental values of elemental analysis: C, 71.69; H, 5.53; F, 9.19; N, 4.52; Si, 9.06.

[0454] Synthesis Example B32:

[0455] The synthesis method was similar to that of B24, a yellow solid with a yield of 83%. Mass spectrometry: m / z 1526.60, experimental values of elemental analysis: C, 67.58; H, 6.59; F, 7.46; N, 3.67; Si, 14.70.

[0456] Synthesis Example B35:

[0457] The synthesis method was similar to that of B24, a yellow solid with a yield of 89%. Mass spectrometry: m / z 1254.41, experimental values of elemental analysis: C, 82.28; H, 4.18; F, 9.08; N, 4.46.

[0458] Synthesis Example B47:

[0459] Weigh intermediate 11 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound B47 by column chromatography, a yellow solid with a yield of 63%. Mass spectrometry: m / z 1143.47, experimental values of elemental analysis: C, 85.03; H, 5.11; B, 0.94; N, 6.12; O, 2.80.

[0460] Synthesis Example B70:

[0461] Weigh intermediate 12 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound B70 by column chromatography, which is a yellow solid with a yield of 63%. Mass spectrum: m / z 1186.46, elemental analysis experimental values: C, 81.95; H, 4.92; B, 0.91; F, 4.80; N, 4.72; O, 2.70.

[0462] Synthesis Example B93:

[0463] Weigh intermediate 13 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound B93 by column chromatography, which is a yellow solid with a yield of 58%. Mass spectrum: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0464] Synthesis Example B116:

[0465] Weigh intermediate 14 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound B116 by column chromatography, which is a yellow solid with a yield of 55%. Mass spectrum: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0466] Synthesis Example B139:

[0467] Weigh intermediate 15 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound B139 by column chromatography, which is a yellow solid with a yield of 59%. Mass spectrum: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0468] Synthesis Example B162:

[0469] Intermediate 16 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound B162 as a yellow solid with a yield of 61%. Mass spectrometry: m / z 1000.30, elemental analysis experimental values: C, 81.59; H, 3.93; F, 5.69; N, 5.60; O, 3.20.

[0470] Synthesis of intermediate 17:

[0471]

[0472] 1,3-Dibromo-2,4,6-trifluoro-5-trifluoromethylbenzene (10 g, 27.94 mmol) and 4-cyanophenylboronic acid (9.03 g, 61.47 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.61 g, 1.59 mmol) and 20 mL of aqueous potassium carbonate solution (7.72 g, 63.51 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain intermediate 17 as a white solid. The weight was 7.3 g, and the yield was 65%.

[0473] Synthesis of intermediates 18 - 24:

[0474]

[0475] The synthesis method was similar to that of intermediate 17. Intermediates 18 - 24 were all white solids, and the yields were 61%, 40%, 45%, 50%, 48%, 55%, and 61% respectively.

[0476] Synthesis example C1:

[0477] Intermediate 17 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound C1 as a yellow solid with a yield of 83%. Mass spectrometry: m / z 843.26, elemental analysis experimental values: C, 81.13; H, 3.82; F, 6.75; N, 8.30.

[0478] Synthesis example C2:

[0479] The synthesis method was similar to that of C1, and the product was a yellow solid with a yield of 79%. Mass spectrometry: m / z 885.31, elemental analysis experimental values: C, 81.34; H, 4.32; F, 6.43; N, 7.90.

[0480] Synthesis Example C3:

[0481] The synthesis method is similar to that of C1, yellow solid, yield 70%. Mass spectrometry: m / z 927.35, experimental values of elemental analysis: C, 81.53; H, 4.78; F, 6.14; N, 7.55.

[0482] Synthesis Example C4:

[0483] The synthesis method is similar to that of C1, yellow solid, yield 72%. Mass spectrometry: m / z 969.40, experimental values of elemental analysis: C, 81.71; H, 5.20; F, 5.87; N, 7.22.

[0484] Synthesis Example C5:

[0485] The synthesis method is similar to that of C1, yellow solid, yield 71%. Mass spectrometry: m / z 1095.54, experimental values of elemental analysis: C, 82.16; H, 6.25; F, 5.20; N, 6.39.

[0486] Synthesis Example C6:

[0487] The synthesis method is similar to that of C1, yellow solid, yield 78%. Mass spectrometry: m / z 1011.45, experimental values of elemental analysis: C, 81.87; H, 5.58; F, 5.63; N, 6.92.

[0488] Synthesis Example C7:

[0489] The synthesis method is similar to that of C1, yellow solid, yield 79%. Mass spectrometry: m / z 1179.64, experimental values of elemental analysis: C, 82.41; H, 6.83; F, 4.83; N, 5.93.

[0490] Synthesis Example C8:

[0491] The synthesis method is similar to that of C1, yellow solid, yield 78%. Mass spectrometry: m / z 1059.38, experimental values of elemental analysis: C, 74.75; H, 5.32; F, 5.37; N, 6.60; Si, 7.95

[0492] Synthesis Example C9:

[0493] The synthesis method is similar to that of C1, yellow solid, yield 79%. Mass spectrometry: m / z 1261.48, experimental values of elemental analysis: C, 70.37; H, 6.23; F, 4.51; N, 5.55; Si, 13.34.

[0494] Synthesis Example C10:

[0495] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 918.25. Experimental values of elemental analysis: C, 78.42; H, 3.18; F, 6.20; N, 12.19.

[0496] Synthesis Example C11:

[0497] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 993.23. Experimental values of elemental analysis: C, 76.13; H, 2.64; F, 5.73; N, 15.50.

[0498] Synthesis Example C12:

[0499] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 76%. Mass spectrometry: m / z 1071.35. Experimental values of elemental analysis: C, 84.02; H, 4.14; F, 5.32; N, 6.53.

[0500] Synthesis Example C13:

[0501] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1299.45. Experimental values of elemental analysis: C, 85.89; H, 4.34; F, 4.38; N, 5.39.

[0502] Synthesis Example C14:

[0503] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1047.22. Experimental values of elemental analysis: C, 68.77; H, 2.79; F, 21.76; N, 6.68.

[0504] Synthesis Example C15:

[0505] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 1251.19. Experimental values of elemental analysis: C, 60.44; H, 2.09; F, 31.87; N, 5.59.

[0506] Synthesis Example C16:

[0507] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1197.50. Experimental values of elemental analysis: C, 84.19; H, 5.21; F, 4.76; N, 5.84.

[0508] Synthesis Example C17:

[0509] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1551.73. Experimental values of elemental analysis: C, 85.85; H, 5.97; F, 3.67; N, 4.51.

[0510] Synthesis Example C18:

[0511] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0512] Synthesis Example C19:

[0513] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0514] Synthesis Example C20:

[0515] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0516] Synthesis Example C21:

[0517] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0518] Synthesis Example C22:

[0519] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 81%. Mass spectrum: m / z 891.25. Experimental values of elemental analysis: C, 76.76; H, 3.62; F, 6.39; N, 7.85; O, 5.38

[0520] Synthesis Example C23:

[0521] The synthesis method is similar to that of C1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 939.18. Experimental values of elemental analysis: C, 72.83; H, 3.43; F, 6.06; N, 7.45; S, 10.23.

[0522] Synthesis Example C24:

[0523] Intermediate 18 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound C24 as a yellow solid with a yield of 83%. Mass spectrometry: m / z 929.25, elemental analysis experimental values: C, 73.62; H, 3.47; F, 18.39; N, 4.52.

[0524] Synthesis Example C25:

[0525] The synthesis method was similar to that of C24, obtaining a yellow solid with a yield of 70%. Mass spectrometry: m / z 971.29, elemental analysis experimental values: C, 74.14; H, 3.94; F, 17.59; N, 4.32.

[0526] Synthesis Example C26:

[0527] The synthesis method was similar to that of C24, obtaining a yellow solid with a yield of 71%. Mass spectrometry: m / z 1013.34, elemental analysis experimental values: C, 74.62; H, 4.37; F, 16.86; N, 4.14.

[0528] Synthesis Example C27:

[0529] The synthesis method was similar to that of C24, obtaining a yellow solid with a yield of 73%. Mass spectrometry: m / z 1055.39, elemental analysis experimental values: C, 75.06; H, 4.77; F, 16.19; N, 3.98.

[0530] Synthesis Example C28:

[0531] The synthesis method was similar to that of C24, obtaining a yellow solid with a yield of 69%. Mass spectrometry: m / z 1181.53, elemental analysis experimental values: C, 76.19; H, 5.80; F, 14.46; N, 3.55

[0532] Synthesis Example C29:

[0533] The synthesis method was similar to that of C24, obtaining a yellow solid with a yield of 67%. Mass spectrometry: m / z 1097.43, elemental analysis experimental values: C, 75.46; H, 5.14; F, 15.57; N, 3.83

[0534] Synthesis Example C30:

[0535] The synthesis method was similar to that of C24, obtaining a yellow solid with a yield of 66%. Mass spectrometry: m / z 1265.62, elemental analysis experimental values: C, 76.82; H, 6.37; F, 13.50; N, 3.32

[0536] Synthesis Example C31:

[0537] The synthesis method is similar to that of C24, yellow solid, yield 80%. Mass spectrometry: m / z 1145.36, experimental values of elemental analysis: C, 69.15; H, 4.92; F, 14.91; N, 3.67; Si, 7.35

[0538] Synthesis Example C32:

[0539] The synthesis method is similar to that of C24, yellow solid, yield 73%. Mass spectrometry: m / z 1347.47, experimental values of elemental analysis: C, 65.89; H, 5.83; F, 12.68; N, 3.12; Si, 12.49

[0540] Synthesis Example C33:

[0541] The synthesis method is similar to that of C24, yellow solid, yield 72%. Mass spectrometry: m / z 1004.23, experimental values of elemental analysis: C, 71.71; H, 2.91; F, 17.01; N, 8.36

[0542] Synthesis Example C34:

[0543] The synthesis method is similar to that of C24, yellow solid, yield 71%. Mass spectrometry: m / z 1079.22, experimental values of elemental analysis: C, 70.07; H, 2.43; F, 15.83; N, 11.67

[0544] Synthesis Example C35:

[0545] The synthesis method is similar to that of C24, yellow solid, yield 69%. Mass spectrometry: m / z 1157.34, experimental values of elemental analysis: C, 77.78; H, 3.83; F, 14.76; N, 3.63

[0546] Synthesis Example C36:

[0547] The synthesis method is similar to that of C24, yellow solid, yield 59%. Mass spectrometry: m / z 1385.43, experimental values of elemental analysis: C, 80.57; H, 4.07; F, 12.33; N, 3.03

[0548] Synthesis Example C37:

[0549] The synthesis method is similar to that of C24, yellow solid, yield 58%. Mass spectrometry: m / z 1133.21, experimental values of elemental analysis: C, 63.56; H, 2.58; F, 30.16; N, 3.71

[0550] Synthesis Example C38:

[0551] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 67%. Mass spectrum: m / z 1337.17, Experimental values of elemental analysis: C, 56.56; H, 1.96; F, 38.34; N, 3.14

[0552] Synthesis Example C39:

[0553] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1283.48, Experimental values of elemental analysis: C, 78.55; H, 4.87; F, 13.31; N, 3.27

[0554] Synthesis Example C40:

[0555] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1637.71, Experimental values of elemental analysis: C, 81.35; H, 5.66; F, 10.43; N, 2.56

[0556] Synthesis Example C41:

[0557] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0558] Synthesis Example C42:

[0559] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0560] Synthesis Example C43:

[0561] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 82%. Mass spectrum: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0562] Synthesis Example C44:

[0563] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0564] Synthesis Example C45:

[0565] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 977.23. Experimental values of elemental analysis: C, 70.01; H, 3.30; F, 17.49; N, 4.30; O, 4.91

[0566] Synthesis Example C46:

[0567] The synthesis method is similar to that of C24. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1025.16. Experimental values of elemental analysis: C, 66.72; H, 3.14; F, 16.66; N, 4.10; S, 9.37

[0568] Synthesis Example C47:

[0569] Weigh intermediate 19 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound C47 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1401.60. Experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56

[0570] Synthesis Example C52:

[0571] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1569.79. Experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07

[0572] Synthesis Example C53:

[0573] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 74%. Mass spectrometry: m / z 1737.97. Experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68

[0574] Synthesis Example C54:

[0575] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1617.72. Experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20

[0576] Synthesis Example C55:

[0577] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1833.83. Experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[0578] Synthesis Example C58:

[0579] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1629.69. Experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[0580] Synthesis Example C59:

[0581] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[0582] Synthesis Example C60:

[0583] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[0584] Synthesis Example C61:

[0585] The synthesis method is similar to that of C47. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[0586] Synthesis Example C70:

[0587] Weigh intermediate 20 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound C70 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60. Experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[0588] Synthesis Example C75:

[0589] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1569.79. Experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[0590] Synthesis Example C76

[0591] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1737.97. Experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[0592] Synthesis Example C77:

[0593] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 68%. Mass spectrum: m / z 1617.72. Experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[0594] Synthesis Example C78:

[0595] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 66%. Mass spectrum: m / z 1833.83. Experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[0596] Synthesis Example C81:

[0597] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1629.69. Experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[0598] Synthesis Example C82:

[0599] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[0600] Synthesis Example C83:

[0601] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[0602] Synthesis Example C84:

[0603] The synthesis method is similar to that of C70. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[0604] Synthesis Example C93:

[0605] Weigh intermediate 21 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound C93 by column chromatography. It is a yellow solid with a yield of 85%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[0606] Synthesis Example C94:

[0607] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[0608] Synthesis Example C95:

[0609] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[0610] Synthesis Example C96:

[0611] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[0612] Synthesis Example C97:

[0613] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[0614] Synthesis Example C98:

[0615] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[0616] Synthesis Example C99:

[0617] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[0618] Synthesis Example C100:

[0619] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[0620] Synthesis Example C101:

[0621] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[0622] Synthesis Example C102:

[0623] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[0624] Synthesis Example C103:

[0625] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[0626] Synthesis Example C104:

[0627] The synthesis method is similar to that of C93. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[0628] Synthesis Example C105:

[0629] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[0630] Synthesis Example C106:

[0631] The synthesis method is similar to that of C93, yellow solid, yield 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[0632] Synthesis Example C107:

[0633] The synthesis method is similar to that of C93, yellow solid, yield 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[0634] Synthesis Example C108:

[0635] The synthesis method is similar to that of C93, yellow solid, yield 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[0636] Synthesis Example C109:

[0637] The synthesis method is similar to that of C93, yellow solid, yield 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[0638] Synthesis Example C110:

[0639] The synthesis method is similar to that of C93, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0640] Synthesis Example C111:

[0641] The synthesis method is similar to that of C93, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0642] Synthesis Example C112:

[0643] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0644] Synthesis Example C113:

[0645] The synthesis method is similar to that of C93, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0646] Synthesis Example C114:

[0647] The synthesis method is similar to that of C93, yellow solid, yield 74%. Mass spectrum: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[0648] Synthesis Example C115:

[0649] The synthesis method is similar to that of C93, yellow solid, yield 72%. Mass spectrum: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[0650] Synthesis Example C116:

[0651] Weigh intermediate 22 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound C116 by column chromatography, yellow solid, yield 83%. Mass spectrum: m / z 1029.28, experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[0652] Synthesis Example C117:

[0653] The synthesis method is similar to that of C116, yellow solid, yield 77%. Mass spectrum: m / z 1071.33, experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[0654] Synthesis Example C118:

[0655] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[0656] Synthesis Example C119:

[0657] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[0658] Synthesis Example C120:

[0659] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[0660] Synthesis Example C121:

[0661] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[0662] Synthesis Example C122:

[0663] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[0664] Synthesis Example C123:

[0665] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[0666] Synthesis Example C124:

[0667] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[0668] Synthesis Example C125:

[0669] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[0670] Synthesis Example C126:

[0671] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[0672] Synthesis Example C127:

[0673] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[0674] Synthesis Example C128:

[0675] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[0676] Synthesis Example C129:

[0677] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[0678] Synthesis Example C130:

[0679] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[0680] Synthesis Example C131:

[0681] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[0682] Synthesis Example C132:

[0683] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[0684] Synthesis Example C133:

[0685] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0686] Synthesis Example C134:

[0687] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0688] Synthesis Example C135:

[0689] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0690] Synthesis Example C136:

[0691] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0692] Synthesis Example C137:

[0693] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 74%. Mass spectrometry: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[0694] Synthesis Example C138:

[0695] The synthesis method is similar to that of C116. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[0696] Synthesis Example C139:

[0697] Weigh intermediate 23 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound C139 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[0698] Synthesis Example C140:

[0699] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[0700] Synthesis Example C141:

[0701] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[0702] Synthesis Example C142:

[0703] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[0704] Synthesis Example C143:

[0705] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[0706] Synthesis Example C144:

[0707] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[0708] Synthesis Example C145:

[0709] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[0710] Synthesis Example C146:

[0711] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[0712] Synthesis Example C147:

[0713] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[0714] Synthesis Example C148:

[0715] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[0716] Synthesis Example C149:

[0717] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[0718] Synthesis Example C150:

[0719] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[0720] Synthesis Example C151:

[0721] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[0722] Synthesis Example C152:

[0723] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24, Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[0724] Synthesis Example C153:

[0725] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21, Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[0726] Synthesis Example C154:

[0727] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52, Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[0728] Synthesis Example C155:

[0729] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75, Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[0730] Synthesis Example C156:

[0731] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0732] Synthesis Example C157:

[0733] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0734] Synthesis Example C158:

[0735] The synthesis method is similar to that of C139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0736] Synthesis Example C159:

[0737] The synthesis method is similar to that of C139, a yellow solid with a yield of 79%. Mass spectrometry: m / z 1032.27, elemental analysis experimental values: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0738] Synthesis Example C160:

[0739] The synthesis method is similar to that of C139, a yellow solid with a yield of 74%. Mass spectrometry: m / z 1077.27, elemental analysis experimental values: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[0740] Synthesis Example C161:

[0741] The synthesis method is similar to that of C139, a yellow solid with a yield of 72%. Mass spectrometry: m / z 1125.20, elemental analysis experimental values: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[0742] Synthesis Example C162:

[0743] Weigh intermediate 24 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound C162 by column chromatography, a yellow solid with a yield of 83%. Mass spectrometry: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[0744] Synthesis Example C163:

[0745] The synthesis method is similar to that of C162, a yellow solid with a yield of 77%. Mass spectrometry: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[0746] Synthesis Example C164:

[0747] The synthesis method is similar to that of C162, a yellow solid with a yield of 70%. Mass spectrometry: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[0748] Synthesis Example C165:

[0749] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[0750] Synthesis Example C166:

[0751] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[0752] Synthesis Example C167:

[0753] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[0754] Synthesis Example C168:

[0755] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[0756] Synthesis Example C169:

[0757] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[0758] Synthesis Example C170:

[0759] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[0760] Synthesis Example C171:

[0761] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[0762] Synthesis Example C172:

[0763] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[0764] Synthesis Example C173:

[0765] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[0766] Synthesis Example C174:

[0767] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[0768] Synthesis Example C175:

[0769] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[0770] Synthesis Example C176:

[0771] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[0772] Synthesis Example C177:

[0773] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[0774] Synthesis Example C178:

[0775] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[0776] Synthesis Example C179:

[0777] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0778] Synthesis Example C180:

[0779] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0780] Synthesis Example C181:

[0781] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0782] Synthesis Example C182:

[0783] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0784] Synthesis Example C183:

[0785] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[0786] Synthesis Example C184:

[0787] The synthesis method is similar to that of C162. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[0788] Synthesis of Intermediate 25:

[0789]

[0790] 1,3 - Dibromo - 4,5,6 - trifluoro - 2 - (trifluoromethyl)benzene (10 g, 27.94 mmol), 4 - cyanophenylboronic acid (9.03 g, 61.47 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.61 g, 1.40 mmol) and 20 mL of aqueous potassium carbonate solution (7.72 g, 55.89 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 25, weighing 6.8 g, with a yield of 60%.

[0791] Synthesis of intermediates 26 - 32:

[0792]

[0793] The synthesis method was similar to that of intermediate 25. Intermediates 25 - 32 were all white solids, and their yields were 59%, 58%, 49%, 70%, 66%, 51%, and 47% respectively.

[0794] Synthesis example D1:

[0795] Weigh intermediate 25 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat the mixture to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and purify it by column chromatography to obtain compound D1, a yellow solid, with a yield of 83%. Mass spectrometry: m / z 843.26, elemental analysis experimental values: C, 81.13; H, 3.82; F, 6.75; N, 8.30.

[0796] Synthesis example D2:

[0797] The synthesis method was similar to that of D1, a yellow solid, with a yield of 79%. Mass spectrometry: m / z 885.31, elemental analysis experimental values: C, 81.34; H, 4.32; F, 6.43; N, 7.90.

[0798] Synthesis example D3:

[0799] The synthesis method was similar to that of D1, a yellow solid, with a yield of 70%. Mass spectrometry: m / z 927.35, elemental analysis experimental values: C, 81.53; H, 4.78; F, 6.14; N, 7.55.

[0800] Synthesis example D4:

[0801] The synthesis method was similar to that of D1, a yellow solid, with a yield of 72%. Mass spectrometry: m / z 969.40, elemental analysis experimental values: C, 81.71; H, 5.20; F, 5.87; N, 7.22.

[0802] Synthesis Example D5:

[0803] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 71%. Mass spectrometry: m / z 1095.54. Experimental values of elemental analysis: C, 82.16; H, 6.25; F, 5.20; N, 6.39.

[0804] Synthesis Example D6:

[0805] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 78%. Mass spectrometry: m / z 1011.45. Experimental values of elemental analysis: C, 81.87; H, 5.58; F, 5.63; N, 6.92.

[0806] Synthesis Example D7:

[0807] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1179.64. Experimental values of elemental analysis: C, 82.41; H, 6.83; F, 4.83; N, 5.93.

[0808] Synthesis Example D8:

[0809] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 78%. Mass spectrometry: m / z 1059.38. Experimental values of elemental analysis: C, 74.75; H, 5.32; F, 5.37; N, 6.60; Si, 7.95

[0810] Synthesis Example D9:

[0811] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1261.48. Experimental values of elemental analysis: C, 70.37; H, 6.23; F, 4.51; N, 5.55; Si, 13.34.

[0812] Synthesis Example D10:

[0813] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 918.25. Experimental values of elemental analysis: C, 78.42; H, 3.18; F, 6.20; N, 12.19.

[0814] Synthesis Example D11:

[0815] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 993.23. Experimental values of elemental analysis: C, 76.13; H, 2.64; F, 5.73; N, 15.50.

[0816] Synthesis Example D12:

[0817] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 76%. Mass spectrum: m / z 1071.35. Experimental values of elemental analysis: C, 84.02; H, 4.14; F, 5.32; N, 6.53.

[0818] Synthesis Example D13:

[0819] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1299.45. Experimental values of elemental analysis: C, 85.89; H, 4.34; F, 4.38; N, 5.39.

[0820] Synthesis Example D14:

[0821] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1047.22. Experimental values of elemental analysis: C, 68.77; H, 2.79; F, 21.76; N, 6.68.

[0822] Synthesis Example D15:

[0823] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1251.19. Experimental values of elemental analysis: C, 60.44; H, 2.09; F, 31.87; N, 5.59.

[0824] Synthesis Example D16:

[0825] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1197.50. Experimental values of elemental analysis: C, 84.19; H, 5.21; F, 4.76; N, 5.84.

[0826] Synthesis Example D17:

[0827] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1551.73. Experimental values of elemental analysis: C, 85.85; H, 5.97; F, 3.67; N, 4.51.

[0828] Synthesis Example D18:

[0829] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0830] Synthesis Example D19:

[0831] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0832] Synthesis Example D20:

[0833] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0834] Synthesis Example D21:

[0835] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[0836] Synthesis Example D22:

[0837] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 81%. Mass spectrum: m / z 891.25. Experimental values of elemental analysis: C, 76.76; H, 3.62; F, 6.39; N, 7.85; O, 5.38

[0838] Synthesis Example D23:

[0839] The synthesis method is similar to that of D1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 939.18. Experimental values of elemental analysis: C, 72.83; H, 3.43; F, 6.06; N, 7.45; S, 10.23.

[0840] Synthesis Example D24:

[0841] Weigh intermediate 26 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound D24 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 929.25. Experimental values of elemental analysis: C, 73.62; H, 3.47; F, 18.39; N, 4.52.

[0842] Synthesis Example D25:

[0843] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 971.29. Experimental values of elemental analysis: C, 74.14; H, 3.94; F, 17.59; N, 4.32.

[0844] Synthesis Example D26:

[0845] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 71%. Mass spectrometry: m / z 1013.34. Experimental values of elemental analysis: C, 74.62; H, 4.37; F, 16.86; N, 4.14.

[0846] Synthesis Example D27:

[0847] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 73%. Mass spectrometry: m / z 1055.39. Experimental values of elemental analysis: C, 75.06; H, 4.77; F, 16.19; N, 3.98.

[0848] Synthesis Example D28:

[0849] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 69%. Mass spectrometry: m / z 1181.53. Experimental values of elemental analysis: C, 76.19; H, 5.80; F, 14.46; N, 3.55

[0850] Synthesis Example D29:

[0851] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 67%. Mass spectrometry: m / z 1097.43. Experimental values of elemental analysis: C, 75.46; H, 5.14; F, 15.57; N, 3.83

[0852] Synthesis Example D30:

[0853] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 66%. Mass spectrometry: m / z 1265.62. Experimental values of elemental analysis: C, 76.82; H, 6.37; F, 13.50; N, 3.32

[0854] Synthesis Example D31:

[0855] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 80%. Mass spectrometry: m / z 1145.36. Experimental values of elemental analysis: C, 69.15; H, 4.92; F, 14.91; N, 3.67; Si, 7.35

[0856] Synthesis Example D32:

[0857] The synthesis method was similar to that of D24. It was a yellow solid with a yield of 73%. Mass spectrometry: m / z 1347.47. Experimental values of elemental analysis: C, 65.89; H, 5.83; F, 12.68; N, 3.12; Si, 12.49

[0858] Synthesis Example D33:

[0859] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1004.23. Experimental values of elemental analysis: C, 71.71; H, 2.91; F, 17.01; N, 8.36

[0860] Synthesis Example D34:

[0861] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 71%. Mass spectrometry: m / z 1079.22. Experimental values of elemental analysis: C, 70.07; H, 2.43; F, 15.83; N, 11.67

[0862] Synthesis Example D35:

[0863] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1157.34. Experimental values of elemental analysis: C, 77.78; H, 3.83; F, 14.76; N, 3.63

[0864] Synthesis Example D36:

[0865] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1385.43. Experimental values of elemental analysis: C, 80.57; H, 4.07; F, 12.33; N, 3.03

[0866] Synthesis Example D37:

[0867] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1133.21. Experimental values of elemental analysis: C, 63.56; H, 2.58; F, 30.16; N, 3.71

[0868] Synthesis Example D38:

[0869] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 67%. Mass spectrometry: m / z 1337.17. Experimental values of elemental analysis: C, 56.56; H, 1.96; F, 38.34; N, 3.14

[0870] Synthesis Example D39:

[0871] The synthesis method is similar to that of D24. It is a yellow solid with a yield of 78%. Mass spectrometry: m / z 1283.48. Experimental values of elemental analysis: C, 78.55; H, 4.87; F, 13.31; N, 3.27

[0872] Synthesis Example D40:

[0873] The synthesis method is similar to that of D24, yellow solid, yield 70%. Mass spectrum: m / z 1637.71, experimental values of elemental analysis: C, 81.35; H, 5.66; F, 10.43; N, 2.56

[0874] Synthesis Example D41:

[0875] The synthesis method is similar to that of D24, yellow solid, yield 75%. Mass spectrum: m / z 932.23, experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0876] Synthesis Example D42:

[0877] The synthesis method is similar to that of D24, yellow solid, yield 80%. Mass spectrum: m / z 932.23, experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0878] Synthesis Example D43:

[0879] The synthesis method is similar to that of D24, yellow solid, yield 82%. Mass spectrum: m / z 932.23, experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0880] Synthesis Example D44:

[0881] The synthesis method is similar to that of D24, yellow solid, yield 79%. Mass spectrum: m / z 932.23, experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[0882] Synthesis Example D45:

[0883] The synthesis method is similar to that of D24, yellow solid, yield 79%. Mass spectrum: m / z 977.23, experimental values of elemental analysis: C, 70.01; H, 3.30; F, 17.49; N, 4.30; O, 4.91

[0884] Synthesis Example D46:

[0885] The synthesis method is similar to that of D24, yellow solid, yield 75%. Mass spectrum: m / z 1025.16, experimental values of elemental analysis: C, 66.72; H, 3.14; F, 16.66; N, 4.10; S, 9.37

[0886] Synthesis Example D47:

[0887] Intermediate 27 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound D47 as a yellow solid with a yield of 83%. Mass spectrometry: m / z 1401.60, elemental analysis experimental values: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[0888] Synthesis Example D52:

[0889] The synthesis method was similar to that of D47, obtaining a yellow solid with a yield of 70%. Mass spectrometry: m / z 1569.79, elemental analysis experimental values: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[0890] Synthesis Example D53:

[0891] The synthesis method was similar to that of D47, obtaining a yellow solid with a yield of 74%. Mass spectrometry: m / z 1737.97, elemental analysis experimental values: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[0892] Synthesis Example D54:

[0893] The synthesis method was similar to that of D47, obtaining a yellow solid with a yield of 75%. Mass spectrometry: m / z 1617.72, elemental analysis experimental values: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[0894] Synthesis Example D55:

[0895] The synthesis method was similar to that of D47, obtaining a yellow solid with a yield of 73%. Mass spectrometry: m / z 1833.83, elemental analysis experimental values: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[0896] Synthesis Example D58:

[0897] The synthesis method was similar to that of D47, obtaining a yellow solid with a yield of 69%. Mass spectrometry: m / z 1629.69, elemental analysis experimental values: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[0898] Synthesis Example D59:

[0899] The synthesis method is similar to that of D47, yellow solid, yield 69%. Mass spectrum: m / z 1857.79, experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[0900] Synthesis Example D60:

[0901] The synthesis method is similar to that of D47, yellow solid, yield 78%. Mass spectrum: m / z 1605.56, experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[0902] Synthesis Example D61:

[0903] The synthesis method is similar to that of D47, yellow solid, yield 74%. Mass spectrum: m / z 1809.52, experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[0904] Synthesis Example D70:

[0905] Weigh intermediate 28 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound D70 by column chromatography, yellow solid, yield 83%. Mass spectrum: m / z 1401.60, experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[0906] Synthesis Example D75:

[0907] The synthesis method is similar to that of D70, yellow solid, yield 73%. Mass spectrum: m / z 1569.79, experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[0908] Synthesis Example D76

[0909] The synthesis method is similar to that of D70, yellow solid, yield 70%. Mass spectrum: m / z 1737.97, experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[0910] Synthesis Example D77:

[0911] The synthesis method is similar to that of D70. It is a yellow solid with a yield of 68%. Mass spectrum: m / z 1617.72. Experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[0912] Synthesis Example D78:

[0913] The synthesis method is similar to that of D70. It is a yellow solid with a yield of 66%. Mass spectrum: m / z 1833.83. Experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[0914] Synthesis Example D81:

[0915] The synthesis method is similar to that of D70. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1629.69. Experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[0916] Synthesis Example D82:

[0917] The synthesis method is similar to that of D70. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[0918] Synthesis Example D83:

[0919] The synthesis method is similar to that of D70. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[0920] Synthesis Example D84:

[0921] The synthesis method is similar to that of D70. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[0922] Synthesis Example D93:

[0923] Weigh intermediate 29 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound D93 by column chromatography. It is a yellow solid with a yield of 85%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[0924] Synthesis Example D94:

[0925] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[0926] Synthesis Example D95:

[0927] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[0928] Synthesis Example D96:

[0929] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[0930] Synthesis Example D97:

[0931] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[0932] Synthesis Example D98:

[0933] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[0934] Synthesis Example D99:

[0935] The synthesis method is similar to that of D93, a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66, experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[0936] Synthesis Example D100:

[0937] The synthesis method is similar to that of D93, a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40, experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[0938] Synthesis Example D101:

[0939] The synthesis method is similar to that of D93, a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52, experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[0940] Synthesis Example D102:

[0941] The synthesis method is similar to that of D93, a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27, experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[0942] Synthesis Example D103:

[0943] The synthesis method is similar to that of D93, a yellow solid with a yield of 72%. Mass spectrometry: m / z 1179.25, experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[0944] Synthesis Example D104:

[0945] The synthesis method is similar to that of D93, a yellow solid with a yield of 79%. Mass spectrometry: m / z 1257.38, experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[0946] Synthesis Example D105:

[0947] The synthesis method is similar to that of D93, a yellow solid with a yield of 79%. Mass spectrometry: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[0948] Synthesis Example D106:

[0949] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[0950] Synthesis Example D107:

[0951] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[0952] Synthesis Example D108:

[0953] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[0954] Synthesis Example D109:

[0955] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[0956] Synthesis Example D110:

[0957] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0958] Synthesis Example D111:

[0959] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0960] Synthesis Example D112:

[0961] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0962] Synthesis Example D113:

[0963] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[0964] Synthesis Example D114:

[0965] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[0966] Synthesis Example D115:

[0967] The synthesis method is similar to that of D93. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[0968] Synthesis Example D116:

[0969] Weigh intermediate 30 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound D116 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[0970] Synthesis Example D117:

[0971] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[0972] Synthesis Example D118:

[0973] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[0974] Synthesis Example D119:

[0975] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[0976] Synthesis Example D120:

[0977] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[0978] Synthesis Example D121:

[0979] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[0980] Synthesis Example D122:

[0981] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[0982] Synthesis Example D123:

[0983] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[0984] Synthesis Example D124:

[0985] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[0986] Synthesis Example D125:

[0987] The synthesis method is similar to that of D116. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[0988] Synthesis Example D126:

[0989] The synthesis method is similar to that of D116, a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25, experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[0990] Synthesis Example D127:

[0991] The synthesis method is similar to that of D116, a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38, experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[0992] Synthesis Example D128:

[0993] The synthesis method is similar to that of D116, a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[0994] Synthesis Example D129:

[0995] The synthesis method is similar to that of D116, a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[0996] Synthesis Example D130:

[0997] The synthesis method is similar to that of D116, a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[0998] Synthesis Example D131:

[0999] The synthesis method is similar to that of D116, a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1000] Synthesis Example D132:

[1001] The synthesis method is similar to that of D116, a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1002] Synthesis Example D133:

[1003] The synthesis method is similar to that of D116, a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1004] Synthesis Example D134:

[1005] The synthesis method is similar to that of D116, a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1006] Synthesis Example D135:

[1007] The synthesis method is similar to that of D116, a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1008] Synthesis Example D136:

[1009] The synthesis method is similar to that of D116, a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1010] Synthesis Example D137:

[1011] The synthesis method is similar to that of D116, a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1012] Synthesis Example D138:

[1013] The synthesis method is similar to that of D116, a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1014] Synthesis Example D139:

[1015] Weigh intermediate 31 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound D139 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1016] Synthesis Example D140:

[1017] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1018] Synthesis Example D141:

[1019] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1020] Synthesis Example D142:

[1021] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1022] Synthesis Example D143:

[1023] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1024] Synthesis Example D144:

[1025] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1026] Synthesis Example D145:

[1027] The synthesis method is similar to that of D139, yellow solid, yield 59%. Mass spectrum: m / z 1365.66, experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1028] Synthesis Example D146:

[1029] The synthesis method is similar to that of D139, yellow solid, yield 61%. Mass spectrum: m / z 1245.40, experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1030] Synthesis Example D147:

[1031] The synthesis method is similar to that of D139, yellow solid, yield 63%. Mass spectrum: m / z 1461.52, experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1032] Synthesis Example D148:

[1033] The synthesis method is similar to that of D139, yellow solid, yield 73%. Mass spectrum: m / z 1104.27, experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1034] Synthesis Example D149:

[1035] The synthesis method is similar to that of D139, yellow solid, yield 72%. Mass spectrum: m / z 1179.25, experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1036] Synthesis Example D150:

[1037] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1257.38, experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1038] Synthesis Example D151:

[1039] The synthesis method is similar to that of D139, yellow solid, yield 79%. Mass spectrum: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1040] Synthesis Example D152:

[1041] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1042] Synthesis Example D153:

[1043] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1044] Synthesis Example D154:

[1045] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1046] Synthesis Example D155:

[1047] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1048] Synthesis Example D156:

[1049] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1050] Synthesis Example D157:

[1051] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1052] Synthesis Example D158:

[1053] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1054] Synthesis Example D159:

[1055] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1056] Synthesis Example D160:

[1057] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1058] Synthesis Example D161:

[1059] The synthesis method is similar to that of D139. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1060] Synthesis Example D162:

[1061] Weigh intermediate 32 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound D162 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1062] Synthesis Example D163:

[1063] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1064] Synthesis Example D164:

[1065] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1066] Synthesis Example D165:

[1067] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1068] Synthesis Example D166:

[1069] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1070] Synthesis Example D167:

[1071] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1072] Synthesis Example D168:

[1073] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1074] Synthesis Example D169:

[1075] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1076] Synthesis Example D170:

[1077] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1078] Synthesis Example D171:

[1079] The synthesis method is similar to that of D162. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1080] Synthesis Example D172:

[1081] The synthesis method is similar to that of D162, a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25, experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1082] Synthesis Example D173:

[1083] The synthesis method is similar to that of D162, a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38, experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1084] Synthesis Example D174:

[1085] The synthesis method is similar to that of D162, a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1086] Synthesis Example D175:

[1087] The synthesis method is similar to that of D162, a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1088] Synthesis Example D176:

[1089] The synthesis method is similar to that of D162, a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1090] Synthesis Example D177:

[1091] The synthesis method is similar to that of D162, a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1092] Synthesis Example D178:

[1093] The synthesis method is similar to that of D162, a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1094] Synthesis Example D179:

[1095] The synthesis method is similar to that of D162, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1096] Synthesis Example D180:

[1097] The synthesis method is similar to that of D162, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1098] Synthesis Example D181:

[1099] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1100] Synthesis Example D182:

[1101] The synthesis method is similar to that of D162, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1102] Synthesis Example D183:

[1103] The synthesis method is similar to that of D162, yellow solid, yield 74%. Mass spectrum: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1104] Synthesis Example D184:

[1105] The synthesis method is similar to that of D162, yellow solid, yield 72%. Mass spectrum: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1106] Synthesis of Intermediate 33:

[1107]

[1108] 1,4-Dibromo-2,3,5-trifluoro-6-(trifluoromethyl)benzene (10 g, 27.94 mmol), 4-cyanophenylboronic acid (13.27 g, 61.47 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.61 g, 1.40 mmol) and 20 mL of aqueous potassium carbonate solution (7.72 g, 55.89 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 33, weighing 7.0 g, with a yield of 62%.

[1109] Synthesis of intermediates 34 - 40:

[1110]

[1111] The synthesis method was similar to that of intermediate 33. Intermediates 34 - 40 were all white solids, with yields of 69%, 74%, 59%, 72%, 76%, 61%, and 58% respectively.

[1112] Synthesis example E1:

[1113] Intermediate 33 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound E1, a yellow solid, with a yield of 83%. Mass spectrometry: m / z 843.26, elemental analysis experimental values: C, 81.13; H, 3.82; F, 6.75; N, 8.30.

[1114] Synthesis example E2:

[1115] The synthesis method was similar to that of E1, a yellow solid, with a yield of 79%. Mass spectrometry: m / z 885.31, elemental analysis experimental values: C, 81.34; H, 4.32; F, 6.43; N, 7.90.

[1116] Synthesis example E3:

[1117] The synthesis method was similar to that of E1, a yellow solid, with a yield of 70%. Mass spectrometry: m / z 927.35, elemental analysis experimental values: C, 81.53; H, 4.78; F, 6.14; N, 7.55.

[1118] Synthesis example E4:

[1119] The synthesis method was similar to that of E1, a yellow solid, with a yield of 72%. Mass spectrometry: m / z 969.40, elemental analysis experimental values: C, 81.71; H, 5.20; F, 5.87; N, 7.22.

[1120] Synthesis Example E5:

[1121] The synthesis method is similar to that of E1, yellow solid, yield 71%. Mass spectrum: m / z 1095.54, experimental values of elemental analysis: C, 82.16; H, 6.25; F, 5.20; N, 6.39.

[1122] Synthesis Example E6:

[1123] The synthesis method is similar to that of E1, yellow solid, yield 78%. Mass spectrum: m / z 1011.45, experimental values of elemental analysis: C, 81.87; H, 5.58; F, 5.63; N, 6.92.

[1124] Synthesis Example E7:

[1125] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 1179.64, experimental values of elemental analysis: C, 82.41; H, 6.83; F, 4.83; N, 5.93.

[1126] Synthesis Example E8:

[1127] The synthesis method is similar to that of E1, yellow solid, yield 78%. Mass spectrum: m / z 1059.38, experimental values of elemental analysis: C, 74.75; H, 5.32; F, 5.37; N, 6.60; Si, 7.95

[1128] Synthesis Example E9:

[1129] The synthesis method is similar to that of E1, yellow solid, yield 79%. Mass spectrum: m / z 1261.48, experimental values of elemental analysis: C, 70.37; H, 6.23; F, 4.51; N, 5.55; Si, 13.34.

[1130] Synthesis Example E10:

[1131] The synthesis method is similar to that of E1, yellow solid, yield 70%. Mass spectrum: m / z 918.25, experimental values of elemental analysis: C, 78.42; H, 3.18; F, 6.20; N, 12.19.

[1132] Synthesis Example E11:

[1133] The synthesis method is similar to that of E1, yellow solid, yield 73%. Mass spectrum: m / z 993.23, experimental values of elemental analysis: C, 76.13; H, 2.64; F, 5.73; N, 15.50.

[1134] Synthesis Example E12:

[1135] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 76%. Mass spectrometry: m / z 1071.35. Experimental values of elemental analysis: C, 84.02; H, 4.14; F, 5.32; N, 6.53.

[1136] Synthesis Example E13:

[1137] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1299.45. Experimental values of elemental analysis: C, 85.89; H, 4.34; F, 4.38; N, 5.39.

[1138] Synthesis Example E14:

[1139] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1047.22. Experimental values of elemental analysis: C, 68.77; H, 2.79; F, 21.76; N, 6.68.

[1140] Synthesis Example E15:

[1141] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 1251.19. Experimental values of elemental analysis: C, 60.44; H, 2.09; F, 31.87; N, 5.59.

[1142] Synthesis Example E16:

[1143] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1197.50. Experimental values of elemental analysis: C, 84.19; H, 5.21; F, 4.76; N, 5.84.

[1144] Synthesis Example E17:

[1145] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1551.73. Experimental values of elemental analysis: C, 85.85; H, 5.97; F, 3.67; N, 4.51.

[1146] Synthesis Example E18:

[1147] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1148] Synthesis Example E19:

[1149] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1150] Synthesis Example E20:

[1151] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1152] Synthesis Example E21:

[1153] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1154] Synthesis Example E22:

[1155] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 81%. Mass spectrum: m / z 891.25. Experimental values of elemental analysis: C, 76.76; H, 3.62; F, 6.39; N, 7.85; O, 5.38

[1156] Synthesis Example E23:

[1157] The synthesis method is similar to that of E1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 939.18. Experimental values of elemental analysis: C, 72.83; H, 3.43; F, 6.06; N, 7.45; S, 10.23.

[1158] Synthesis Example E24:

[1159] Weigh intermediate 34 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound E24 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 929.25. Experimental values of elemental analysis: C, 73.62; H, 3.47; F, 18.39; N, 4.52.

[1160] Synthesis Example E25:

[1161] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 971.29. Experimental values of elemental analysis: C, 74.14; H, 3.94; F, 17.59; N, 4.32.

[1162] Synthesis Example E26:

[1163] The synthesis method was similar to that of E24, a yellow solid, with a yield of 71%. Mass spectrum: m / z 1013.34, experimental values of elemental analysis: C, 74.62; H, 4.37; F, 16.86; N, 4.14.

[1164] Synthesis Example E27:

[1165] The synthesis method was similar to that of E24, a yellow solid, with a yield of 73%. Mass spectrum: m / z 1055.39, experimental values of elemental analysis: C, 75.06; H, 4.77; F, 16.19; N, 3.98.

[1166] Synthesis Example E28:

[1167] The synthesis method was similar to that of E24, a yellow solid, with a yield of 69%. Mass spectrum: m / z 1181.53, experimental values of elemental analysis: C, 76.19; H, 5.80; F, 14.46; N, 3.55

[1168] Synthesis Example E29:

[1169] The synthesis method was similar to that of E24, a yellow solid, with a yield of 67%. Mass spectrum: m / z 1097.43, experimental values of elemental analysis: C, 75.46; H, 5.14; F, 15.57; N, 3.83

[1170] Synthesis Example E30:

[1171] The synthesis method was similar to that of E24, a yellow solid, with a yield of 66%. Mass spectrum: m / z 1265.62, experimental values of elemental analysis: C, 76.82; H, 6.37; F, 13.50; N, 3.32

[1172] Synthesis Example E31:

[1173] The synthesis method was similar to that of E24, a yellow solid, with a yield of 80%. Mass spectrum: m / z 1145.36, experimental values of elemental analysis: C, 69.15; H, 4.92; F, 14.91; N, 3.67; Si, 7.35

[1174] Synthesis Example E32:

[1175] The synthesis method was similar to that of E24, a yellow solid, with a yield of 73%. Mass spectrum: m / z 1347.47, experimental values of elemental analysis: C, 65.89; H, 5.83; F, 12.68; N, 3.12; Si, 12.49

[1176] Synthesis Example E33:

[1177] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1004.23. Experimental values of elemental analysis: C, 71.71; H, 2.91; F, 17.01; N, 8.36

[1178] Synthesis Example E34:

[1179] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1079.22. Experimental values of elemental analysis: C, 70.07; H, 2.43; F, 15.83; N, 11.67

[1180] Synthesis Example E35:

[1181] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1157.34. Experimental values of elemental analysis: C, 77.78; H, 3.83; F, 14.76; N, 3.63

[1182] Synthesis Example E36:

[1183] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1385.43. Experimental values of elemental analysis: C, 80.57; H, 4.07; F, 12.33; N, 3.03

[1184] Synthesis Example E37:

[1185] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1133.21. Experimental values of elemental analysis: C, 63.56; H, 2.58; F, 30.16; N, 3.71

[1186] Synthesis Example E38:

[1187] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 67%. Mass spectrum: m / z 1337.17. Experimental values of elemental analysis: C, 56.56; H, 1.96; F, 38.34; N, 3.14

[1188] Synthesis Example E39:

[1189] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1283.48. Experimental values of elemental analysis: C, 78.55; H, 4.87; F, 13.31; N, 3.27

[1190] Synthesis Example E40:

[1191] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1637.71. Experimental values of elemental analysis: C, 81.35; H, 5.66; F, 10.43; N, 2.56

[1192] Synthesis Example E41:

[1193] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1194] Synthesis Example E42:

[1195] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1196] Synthesis Example E43:

[1197] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 82%. Mass spectrum: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1198] Synthesis Example E44:

[1199] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1200] Synthesis Example E45:

[1201] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 977.23. Experimental values of elemental analysis: C, 70.01; H, 3.30; F, 17.49; N, 4.30; O, 4.91

[1202] Synthesis Example E46:

[1203] The synthesis method is similar to that of E24. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1025.16. Experimental values of elemental analysis: C, 66.72; H, 3.14; F, 16.66; N, 4.10; S, 9.37

[1204] Synthesis Example E47:

[1205] Weigh intermediate 35 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound E47 by column chromatography, which is a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60, elemental analysis experimental values: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[1206] Synthesis Example E52:

[1207] The synthesis method is similar to that of E47, which is a yellow solid with a yield of 70%. Mass spectrum: m / z 1569.79, elemental analysis experimental values: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[1208] Synthesis Example E53:

[1209] The synthesis method is similar to that of E47, which is a yellow solid with a yield of 74%. Mass spectrum: m / z 1737.97, elemental analysis experimental values: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[1210] Synthesis Example E54:

[1211] The synthesis method is similar to that of E47, which is a yellow solid with a yield of 75%. Mass spectrum: m / z 1617.72, elemental analysis experimental values: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[1212] Synthesis Example E55:

[1213] The synthesis method is similar to that of E47, which is a yellow solid with a yield of 73%. Mass spectrum: m / z 1833.83, elemental analysis experimental values: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[1214] Synthesis Example E58:

[1215] The synthesis method is similar to that of E47, which is a yellow solid with a yield of 69%. Mass spectrum: m / z 1629.69, elemental analysis experimental values: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[1216] Synthesis Example E59:

[1217] The synthesis method is similar to that of E47. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[1218] Synthesis Example E60:

[1219] The synthesis method is similar to that of E47. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[1220] Synthesis Example E61:

[1221] The synthesis method is similar to that of E47. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[1222] Synthesis Example E70:

[1223] Weigh intermediate 36 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound E70 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60. Experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[1224] Synthesis Example E75:

[1225] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1569.79. Experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[1226] Synthesis Example E76

[1227] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1737.97. Experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[1228] Synthesis Example E77:

[1229] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 68%. Mass spectrum: m / z 1617.72. Experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[1230] Synthesis Example E78:

[1231] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 66%. Mass spectrum: m / z 1833.83. Experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[1232] Synthesis Example E81:

[1233] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1629.69. Experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[1234] Synthesis Example E82:

[1235] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[1236] Synthesis Example E83:

[1237] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[1238] Synthesis Example E84:

[1239] The synthesis method is similar to that of E70. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[1240] Synthesis Example E93:

[1241] Weigh intermediate 37 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound E93 by column chromatography, which is a yellow solid with a yield of 85%. Mass spectrum: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1242] Synthesis Example E94:

[1243] The synthesis method is similar to that of E93, which is a yellow solid with a yield of 71%. Mass spectrum: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1244] Synthesis Example E95:

[1245] The synthesis method is similar to that of E93, which is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1246] Synthesis Example E96:

[1247] The synthesis method is similar to that of E93, which is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1248] Synthesis Example E97:

[1249] The synthesis method is similar to that of E93, which is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1250] Synthesis Example E98:

[1251] The synthesis method is similar to that of E93, which is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1252] Synthesis Example E99:

[1253] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1254] Synthesis Example E100:

[1255] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1256] Synthesis Example E101:

[1257] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1258] Synthesis Example E102:

[1259] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1260] Synthesis Example E103:

[1261] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1262] Synthesis Example E104:

[1263] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1264] Synthesis Example E105:

[1265] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1266] Synthesis Example E106:

[1267] The synthesis method is similar to that of E93, yellow solid, yield 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1268] Synthesis Example E107:

[1269] The synthesis method is similar to that of E93, yellow solid, yield 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1270] Synthesis Example E108:

[1271] The synthesis method is similar to that of E93, yellow solid, yield 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1272] Synthesis Example E109:

[1273] The synthesis method is similar to that of E93, yellow solid, yield 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1274] Synthesis Example E110:

[1275] The synthesis method is similar to that of E93, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1276] Synthesis Example E111:

[1277] The synthesis method is similar to that of E93, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1278] Synthesis Example E112:

[1279] The synthesis method is similar to that of E93, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1280] Synthesis Example E113:

[1281] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1282] Synthesis Example E114:

[1283] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1284] Synthesis Example E115:

[1285] The synthesis method is similar to that of E93. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1286] Synthesis Example E116:

[1287] Weigh intermediate 38 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound E116 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1288] Synthesis Example E117:

[1289] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1290] Synthesis Example E118:

[1291] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1292] Synthesis Example E119:

[1293] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1294] Synthesis Example E120:

[1295] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1296] Synthesis Example E121:

[1297] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1298] Synthesis Example E122:

[1299] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1300] Synthesis Example E123:

[1301] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1302] Synthesis Example E124:

[1303] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1304] Synthesis Example E125:

[1305] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1306] Synthesis Example E126:

[1307] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1308] Synthesis Example E127:

[1309] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1310] Synthesis Example E128:

[1311] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1312] Synthesis Example E129:

[1313] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1314] Synthesis Example E130:

[1315] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1316] Synthesis Example E131:

[1317] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1318] Synthesis Example E132:

[1319] The synthesis method is similar to that of E116. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1320] Synthesis Example E133:

[1321] The synthesis method is similar to that of E116, a yellow solid with a yield of 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1322] Synthesis Example E134:

[1323] The synthesis method is similar to that of E116, a yellow solid with a yield of 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1324] Synthesis Example E135:

[1325] The synthesis method is similar to that of E116, a yellow solid with a yield of 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1326] Synthesis Example E136:

[1327] The synthesis method is similar to that of E116, a yellow solid with a yield of 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1328] Synthesis Example E137:

[1329] The synthesis method is similar to that of E116, a yellow solid with a yield of 74%. Mass spectrometry: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1330] Synthesis Example E138:

[1331] The synthesis method is similar to that of E116, a yellow solid with a yield of 72%. Mass spectrometry: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1332] Synthesis Example E139:

[1333] Intermediate 39 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound E139 as a yellow solid with a yield of 83%. Mass spectrometry: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1334] Synthesis Example E140:

[1335] The synthesis method was similar to that of E139, and a yellow solid was obtained with a yield of 77%. Mass spectrometry: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1336] Synthesis Example E141:

[1337] The synthesis method was similar to that of E139, and a yellow solid was obtained with a yield of 70%. Mass spectrometry: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1338] Synthesis Example E142:

[1339] The synthesis method was similar to that of E139, and a yellow solid was obtained with a yield of 59%. Mass spectrometry: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1340] Synthesis Example E143:

[1341] The synthesis method was similar to that of E139, and a yellow solid was obtained with a yield of 58%. Mass spectrometry: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1342] Synthesis Example E144:

[1343] The synthesis method was similar to that of E139, and a yellow solid was obtained with a yield of 55%. Mass spectrometry: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1344] Synthesis Example E145:

[1345] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1346] Synthesis Example E146:

[1347] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1348] Synthesis Example E147:

[1349] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1350] Synthesis Example E148:

[1351] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1352] Synthesis Example E149:

[1353] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1354] Synthesis Example E150:

[1355] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1356] Synthesis Example E151:

[1357] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1358] Synthesis Example E152:

[1359] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1360] Synthesis Example E153:

[1361] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1362] Synthesis Example E154:

[1363] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1364] Synthesis Example E155:

[1365] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1366] Synthesis Example E156:

[1367] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1368] Synthesis Example E157:

[1369] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1370] Synthesis Example E158:

[1371] The synthesis method is similar to that of E139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1372] Synthesis Example E159:

[1373] The synthesis method is similar to that of E139, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1374] Synthesis Example E160:

[1375] The synthesis method is similar to that of E139, yellow solid, yield 74%. Mass spectrometry: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1376] Synthesis Example E161:

[1377] The synthesis method is similar to that of E139, yellow solid, yield 72%. Mass spectrometry: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1378] Synthesis Example E162:

[1379] Weigh intermediate 40 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound E162 by column chromatography, yellow solid, yield 83%. Mass spectrometry: m / z 1029.28, experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1380] Synthesis Example E163:

[1381] The synthesis method is similar to that of E162, yellow solid, yield 77%. Mass spectrometry: m / z 1071.33, experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1382] Synthesis Example E164:

[1383] The synthesis method is similar to that of E162, yellow solid, yield 70%. Mass spectrometry: m / z 1113.38, experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1384] Synthesis Example E165:

[1385] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1386] Synthesis Example E166:

[1387] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1388] Synthesis Example E167:

[1389] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1390] Synthesis Example E168:

[1391] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1392] Synthesis Example E169:

[1393] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1394] Synthesis Example E170:

[1395] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1396] Synthesis Example E171:

[1397] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1398] Synthesis Example E172:

[1399] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1400] Synthesis Example E173:

[1401] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1402] Synthesis Example E174:

[1403] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1404] Synthesis Example E175:

[1405] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1406] Synthesis Example E176:

[1407] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1408] Synthesis Example E177:

[1409] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1410] Synthesis Example E178:

[1411] The synthesis method is similar to that of E162. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1412] Synthesis Example E179:

[1413] The synthesis method is similar to that of E162, yellow solid, yield 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1414] Synthesis Example E180:

[1415] The synthesis method is similar to that of E162, yellow solid, yield 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1416] Synthesis Example E181:

[1417] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1418] Synthesis Example E182:

[1419] The synthesis method is similar to that of E162, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1420] Synthesis Example E183:

[1421] The synthesis method is similar to that of E162, yellow solid, yield 74%. Mass spectrometry: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1422] Synthesis Example E184:

[1423] The synthesis method is similar to that of E162, yellow solid, yield 72%. Mass spectrometry: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1424] Synthesis of Intermediate 41:

[1425]

[1426] 1,2-Dibromo-3,4,6-trifluoro-5-trifluoromethylbenzene (10 g, 27.94 mmol), 4-cyanophenylboronic acid (13.27 g, 61.47 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.61 g, 1.40 mmol) and 20 mL of aqueous potassium carbonate solution (7.72 g, 55.89 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 41, weighing 6.5 g, with a yield of 58%.

[1427] Synthesis of intermediates 42 - 48:

[1428]

[1429] The synthesis method was similar to that of intermediate 41. Intermediates 42 - 48 were all white solids, and their yields were 55%, 64%, 58%, 62%, 66%, 51%, and 55% respectively.

[1430] Synthesis example F1:

[1431] Weigh intermediate 41 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat the mixture to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and purify it by column chromatography to obtain compound F1, a yellow solid, with a yield of 83%. Mass spectrometry: m / z 843.26, elemental analysis experimental values: C, 81.13; H, 3.82; F, 6.75; N, 8.30.

[1432] Synthesis example F2:

[1433] The synthesis method was similar to that of F1, a yellow solid, with a yield of 79%. Mass spectrometry: m / z 885.31, elemental analysis experimental values: C, 81.34; H, 4.32; F, 6.43; N, 7.90.

[1434] Synthesis example F3:

[1435] The synthesis method was similar to that of F1, a yellow solid, with a yield of 70%. Mass spectrometry: m / z 927.35, elemental analysis experimental values: C, 81.53; H, 4.78; F, 6.14; N, 7.55.

[1436] Synthesis example F4:

[1437] The synthesis method was similar to that of F1, a yellow solid, with a yield of 72%. Mass spectrometry: m / z 969.40, elemental analysis experimental values: C, 81.71; H, 5.20; F, 5.87; N, 7.22.

[1438] Synthesis Example F5:

[1439] The synthesis method is similar to that of F1, yellow solid, yield 71%. Mass spectrometry: m / z 1095.54, experimental values of elemental analysis: C, 82.16; H, 6.25; F, 5.20; N, 6.39.

[1440] Synthesis Example F6:

[1441] The synthesis method is similar to that of F1, yellow solid, yield 78%. Mass spectrometry: m / z 1011.45, experimental values of elemental analysis: C, 81.87; H, 5.58; F, 5.63; N, 6.92.

[1442] Synthesis Example F7:

[1443] The synthesis method is similar to that of F1, yellow solid, yield 79%. Mass spectrometry: m / z 1179.64, experimental values of elemental analysis: C, 82.41; H, 6.83; F, 4.83; N, 5.93.

[1444] Synthesis Example F8:

[1445] The synthesis method is similar to that of F1, yellow solid, yield 78%. Mass spectrometry: m / z 1059.38, experimental values of elemental analysis: C, 74.75; H, 5.32; F, 5.37; N, 6.60; Si, 7.95

[1446] Synthesis Example F9:

[1447] The synthesis method is similar to that of F1, yellow solid, yield 79%. Mass spectrometry: m / z 1261.48, experimental values of elemental analysis: C, 70.37; H, 6.23; F, 4.51; N, 5.55; Si, 13.34.

[1448] Synthesis Example F10:

[1449] The synthesis method is similar to that of F1, yellow solid, yield 70%. Mass spectrometry: m / z 918.25, experimental values of elemental analysis: C, 78.42; H, 3.18; F, 6.20; N, 12.19.

[1450] Synthesis Example F11:

[1451] The synthesis method is similar to that of F1, yellow solid, yield 73%. Mass spectrometry: m / z 993.23, experimental values of elemental analysis: C, 76.13; H, 2.64; F, 5.73; N, 15.50.

[1452] Synthesis Example F12:

[1453] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 76%. Mass spectrometry: m / z 1071.35. Experimental values of elemental analysis: C, 84.02; H, 4.14; F, 5.32; N, 6.53.

[1454] Synthesis Example F13:

[1455] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1299.45. Experimental values of elemental analysis: C, 85.89; H, 4.34; F, 4.38; N, 5.39.

[1456] Synthesis Example F14:

[1457] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1047.22. Experimental values of elemental analysis: C, 68.77; H, 2.79; F, 21.76; N, 6.68.

[1458] Synthesis Example F15:

[1459] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 1251.19. Experimental values of elemental analysis: C, 60.44; H, 2.09; F, 31.87; N, 5.59.

[1460] Synthesis Example F16:

[1461] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1197.50. Experimental values of elemental analysis: C, 84.19; H, 5.21; F, 4.76; N, 5.84.

[1462] Synthesis Example F17:

[1463] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1551.73. Experimental values of elemental analysis: C, 85.85; H, 5.97; F, 3.67; N, 4.51.

[1464] Synthesis Example F18:

[1465] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1466] Synthesis Example F19:

[1467] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1468] Synthesis Example F20:

[1469] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1470] Synthesis Example F21:

[1471] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1472] Synthesis Example F22:

[1473] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 81%. Mass spectrometry: m / z 891.25. Experimental values of elemental analysis: C, 76.76; H, 3.62; F, 6.39; N, 7.85; O, 5.38

[1474] Synthesis Example F23:

[1475] The synthesis method is similar to that of F1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 939.18. Experimental values of elemental analysis: C, 72.83; H, 3.43; F, 6.06; N, 7.45; S, 10.23.

[1476] Synthesis Example F24:

[1477] Weigh intermediate 42 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F24 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 929.25. Experimental values of elemental analysis: C, 73.62; H, 3.47; F, 18.39; N, 4.52.

[1478] Synthesis Example F25:

[1479] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 971.29. Experimental values of elemental analysis: C, 74.14; H, 3.94; F, 17.59; N, 4.32.

[1480] Synthesis Example F26:

[1481] The synthesis method is similar to that of F24, yellow solid, yield 71%. Mass spectrum: m / z 1013.34, experimental values of elemental analysis: C, 74.62; H, 4.37; F, 16.86; N, 4.14.

[1482] Synthesis Example F27:

[1483] The synthesis method is similar to that of F24, yellow solid, yield 73%. Mass spectrum: m / z 1055.39, experimental values of elemental analysis: C, 75.06; H, 4.77; F, 16.19; N, 3.98.

[1484] Synthesis Example F28:

[1485] The synthesis method is similar to that of F24, yellow solid, yield 69%. Mass spectrum: m / z 1181.53, experimental values of elemental analysis: C, 76.19; H, 5.80; F, 14.46; N, 3.55

[1486] Synthesis Example F29:

[1487] The synthesis method is similar to that of F24, yellow solid, yield 67%. Mass spectrum: m / z 1097.43, experimental values of elemental analysis: C, 75.46; H, 5.14; F, 15.57; N, 3.83

[1488] Synthesis Example F30:

[1489] The synthesis method is similar to that of F24, yellow solid, yield 66%. Mass spectrum: m / z 1265.62, experimental values of elemental analysis: C, 76.82; H, 6.37; F, 13.50; N, 3.32

[1490] Synthesis Example F31:

[1491] The synthesis method is similar to that of F24, yellow solid, yield 80%. Mass spectrum: m / z 1145.36, experimental values of elemental analysis: C, 69.15; H, 4.92; F, 14.91; N, 3.67; Si, 7.35

[1492] Synthesis Example F32:

[1493] The synthesis method is similar to that of F24, yellow solid, yield 73%. Mass spectrum: m / z 1347.47, experimental values of elemental analysis: C, 65.89; H, 5.83; F, 12.68; N, 3.12; Si, 12.49

[1494] Synthesis Example F33:

[1495] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1004.23. Experimental values of elemental analysis: C, 71.71; H, 2.91; F, 17.01; N, 8.36

[1496] Synthesis Example F34:

[1497] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1079.22. Experimental values of elemental analysis: C, 70.07; H, 2.43; F, 15.83; N, 11.67

[1498] Synthesis Example F35:

[1499] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1157.34. Experimental values of elemental analysis: C, 77.78; H, 3.83; F, 14.76; N, 3.63

[1500] Synthesis Example F36:

[1501] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1385.43. Experimental values of elemental analysis: C, 80.57; H, 4.07; F, 12.33; N, 3.03

[1502] Synthesis Example F37:

[1503] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1133.21. Experimental values of elemental analysis: C, 63.56; H, 2.58; F, 30.16; N, 3.71

[1504] Synthesis Example F38:

[1505] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 67%. Mass spectrum: m / z 1337.17. Experimental values of elemental analysis: C, 56.56; H, 1.96; F, 38.34; N, 3.14

[1506] Synthesis Example F39:

[1507] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1283.48. Experimental values of elemental analysis: C, 78.55; H, 4.87; F, 13.31; N, 3.27

[1508] Synthesis Example F40:

[1509] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1637.71. Experimental values of elemental analysis: C, 81.35; H, 5.66; F, 10.43; N, 2.56

[1510] Synthesis Example F41:

[1511] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1512] Synthesis Example F42:

[1513] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1514] Synthesis Example F43:

[1515] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 82%. Mass spectrometry: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1516] Synthesis Example F44:

[1517] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 932.23. Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1518] Synthesis Example F45:

[1519] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 977.23. Experimental values of elemental analysis: C, 70.01; H, 3.30; F, 17.49; N, 4.30; O, 4.91

[1520] Synthesis Example F46:

[1521] The synthesis method is similar to that of F24. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1025.16. Experimental values of elemental analysis: C, 66.72; H, 3.14; F, 16.66; N, 4.10; S, 9.37

[1522] Synthesis Example F47:

[1523] Weigh intermediate 43 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F47 by column chromatography, which is a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60, experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[1524] Synthesis Example F52:

[1525] The synthesis method is similar to that of F47, which is a yellow solid with a yield of 70%. Mass spectrum: m / z 1569.79, experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[1526] Synthesis Example F53:

[1527] The synthesis method is similar to that of F47, which is a yellow solid with a yield of 74%. Mass spectrum: m / z 1737.97, experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[1528] Synthesis Example F54:

[1529] The synthesis method is similar to that of F47, which is a yellow solid with a yield of 75%. Mass spectrum: m / z 1617.72, experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[1530] Synthesis Example F55:

[1531] The synthesis method is similar to that of F47, which is a yellow solid with a yield of 73%. Mass spectrum: m / z 1833.83, experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[1532] Synthesis Example F58:

[1533] The synthesis method is similar to that of F47, which is a yellow solid with a yield of 69%. Mass spectrum: m / z 1629.69, experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[1534] Synthesis Example F59:

[1535] The synthesis method is similar to that of F47. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[1536] Synthesis Example F60:

[1537] The synthesis method is similar to that of F47. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[1538] Synthesis Example F61:

[1539] The synthesis method is similar to that of F47. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[1540] Synthesis Example F70:

[1541] Weigh intermediate 44 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F70 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60. Experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[1542] Synthesis Example F75:

[1543] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1569.79. Experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[1544] Synthesis Example F76

[1545] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1737.97. Experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[1546] Synthesis Example F77:

[1547] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 68%. Mass spectrometry: m / z 1617.72. Experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[1548] Synthesis Example F78:

[1549] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 66%. Mass spectrometry: m / z 1833.83. Experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[1550] Synthesis Example F81:

[1551] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 77%. Mass spectrometry: m / z 1629.69. Experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[1552] Synthesis Example F82:

[1553] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 77%. Mass spectrometry: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[1554] Synthesis Example F83:

[1555] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 74%. Mass spectrometry: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[1556] Synthesis Example F84:

[1557] The synthesis method is similar to that of F70. It is a yellow solid with a yield of 71%. Mass spectrometry: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[1558] Synthesis Example F93:

[1559] Weigh intermediate 45 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F93 by column chromatography, which is a yellow solid with a yield of 85%. Mass spectrum: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1560] Synthesis Example F94:

[1561] The synthesis method is similar to that of F93, which is a yellow solid with a yield of 71%. Mass spectrum: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1562] Synthesis Example F95:

[1563] The synthesis method is similar to that of F93, which is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1564] Synthesis Example F96:

[1565] The synthesis method is similar to that of F93, which is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1566] Synthesis Example F97:

[1567] The synthesis method is similar to that of F93, which is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1568] Synthesis Example F98:

[1569] The synthesis method is similar to that of F93, which is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1570] Synthesis Example F99:

[1571] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1572] Synthesis Example F100:

[1573] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1574] Synthesis Example F101:

[1575] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1576] Synthesis Example F102:

[1577] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1578] Synthesis Example F103:

[1579] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1580] Synthesis Example F104:

[1581] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1582] Synthesis Example F105:

[1583] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1584] Synthesis Example F106:

[1585] The synthesis method is similar to that of F93, a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1586] Synthesis Example F107:

[1587] The synthesis method is similar to that of F93, a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1588] Synthesis Example F108:

[1589] The synthesis method is similar to that of F93, a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1590] Synthesis Example F109:

[1591] The synthesis method is similar to that of F93, a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1592] Synthesis Example F110:

[1593] The synthesis method is similar to that of F93, a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1594] Synthesis Example F111:

[1595] The synthesis method is similar to that of F93, a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1596] Synthesis Example F112:

[1597] The synthesis method is similar to that of F93, a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1598] Synthesis Example F113:

[1599] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1600] Synthesis Example F114:

[1601] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 74%. Mass spectrometry: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1602] Synthesis Example F115:

[1603] The synthesis method is similar to that of F93. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1604] Synthesis Example F116:

[1605] Weigh intermediate 46 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F116 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1606] Synthesis Example F117:

[1607] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 77%. Mass spectrometry: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1608] Synthesis Example F118:

[1609] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1610] Synthesis Example F119:

[1611] The synthesis method is similar to that of F116, a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42, experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1612] Synthesis Example F120:

[1613] The synthesis method is similar to that of F116, a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56, experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1614] Synthesis Example F121:

[1615] The synthesis method is similar to that of F116, a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47, experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1616] Synthesis Example F122:

[1617] The synthesis method is similar to that of F116, a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66, experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1618] Synthesis Example F123:

[1619] The synthesis method is similar to that of F116, a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40, experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1620] Synthesis Example F124:

[1621] The synthesis method is similar to that of F116, a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52, experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1622] Synthesis Example F125:

[1623] The synthesis method is similar to that of F116, a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27, experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1624] Synthesis Example F126:

[1625] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1626] Synthesis Example F127:

[1627] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1628] Synthesis Example F128:

[1629] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1630] Synthesis Example F129:

[1631] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1632] Synthesis Example F130:

[1633] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1634] Synthesis Example F131:

[1635] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1636] Synthesis Example F132:

[1637] The synthesis method is similar to that of F116. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1638] Synthesis Example F133:

[1639] The synthesis method is similar to that of F116, yellow solid, yield 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1640] Synthesis Example F134:

[1641] The synthesis method is similar to that of F116, yellow solid, yield 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1642] Synthesis Example F135:

[1643] The synthesis method is similar to that of F116, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1644] Synthesis Example F136:

[1645] The synthesis method is similar to that of F116, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1646] Synthesis Example F137:

[1647] The synthesis method is similar to that of F116, yellow solid, yield 74%. Mass spectrometry: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1648] Synthesis Example F138:

[1649] The synthesis method is similar to that of F116, yellow solid, yield 72%. Mass spectrometry: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1650] Synthesis Example F139:

[1651] Weigh intermediate 47 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F139 by column chromatography, which is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1652] Synthesis Example F140:

[1653] The synthesis method is similar to that of F139, which is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1654] Synthesis Example F141:

[1655] The synthesis method is similar to that of F139, which is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1656] Synthesis Example F142:

[1657] The synthesis method is similar to that of F139, which is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1658] Synthesis Example F143:

[1659] The synthesis method is similar to that of F139, which is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1660] Synthesis Example F144:

[1661] The synthesis method is similar to that of F139, which is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1662] Synthesis Example F145:

[1663] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1664] Synthesis Example F146:

[1665] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1666] Synthesis Example F147:

[1667] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1668] Synthesis Example F148:

[1669] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1670] Synthesis Example F149:

[1671] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1672] Synthesis Example F150:

[1673] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1674] Synthesis Example F151:

[1675] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1676] Synthesis Example F152:

[1677] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24, Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1678] Synthesis Example F153:

[1679] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21, Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1680] Synthesis Example F154:

[1681] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52, Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1682] Synthesis Example F155:

[1683] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75, Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1684] Synthesis Example F156:

[1685] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1686] Synthesis Example F157:

[1687] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27, Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1688] Synthesis Example F158:

[1689] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1690] Synthesis Example F159:

[1691] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1692] Synthesis Example F160:

[1693] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27. Experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1694] Synthesis Example F161:

[1695] The synthesis method is similar to that of F139. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20. Experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1696] Synthesis Example F162:

[1697] Weigh intermediate 48 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound F162 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28. Experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1698] Synthesis Example F163:

[1699] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33. Experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1700] Synthesis Example F164:

[1701] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38. Experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1702] Synthesis Example F165:

[1703] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1704] Synthesis Example F166:

[1705] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1706] Synthesis Example F167:

[1707] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1708] Synthesis Example F168:

[1709] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1710] Synthesis Example F169:

[1711] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1712] Synthesis Example F170:

[1713] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1714] Synthesis Example F171:

[1715] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1716] Synthesis Example F172:

[1717] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1718] Synthesis Example F173:

[1719] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1720] Synthesis Example F174:

[1721] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1722] Synthesis Example F175:

[1723] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1724] Synthesis Example F176:

[1725] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1726] Synthesis Example F177:

[1727] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1728] Synthesis Example F178:

[1729] The synthesis method is similar to that of F162. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1730] Synthesis Example F179:

[1731] The synthesis method is similar to that of F162, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1732] Synthesis Example F180:

[1733] The synthesis method is similar to that of F162, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1734] Synthesis Example F181:

[1735] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1736] Synthesis Example F182:

[1737] The synthesis method is similar to that of F162, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1738] Synthesis Example F183:

[1739] The synthesis method is similar to that of F162, yellow solid, yield 74%. Mass spectrum: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1740] Synthesis Example F184:

[1741] The synthesis method is similar to that of F162, yellow solid, yield 72%. Mass spectrum: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1742] Synthesis of Intermediate 49:

[1743]

[1744] 1,2-Dibromo-3,4,5-trifluoro-6-trifluoromethylbenzene (10 g, 27.94 mmol), 4-cyanophenylboronic acid (13.27 g, 61.47 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.61 g, 1.40 mmol) and 20 mL of aqueous potassium carbonate solution (7.72 g, 55.89 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 49, weighing 7.0 g, with a yield of 62%.

[1745] Synthesis of intermediates 50 - 56:

[1746]

[1747] The synthesis method was similar to that of intermediate 49. Intermediates 50 - 56 were all white solids, and their yields were 60%, 71%, 68%, 59%, 74%, 69%, and 66% respectively.

[1748] Synthesis example G1:

[1749] Weigh intermediate 49 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat the mixture to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and purify it by column chromatography to obtain compound G1, a yellow solid, with a yield of 83%. Mass spectrometry: m / z 843.26, elemental analysis experimental values: C, 81.13; H, 3.82; F, 6.75; N, 8.30.

[1750] Synthesis example G2:

[1751] The synthesis method was similar to that of G1, a yellow solid, with a yield of 79%. Mass spectrometry: m / z 885.31, elemental analysis experimental values: C, 81.34; H, 4.32; F, 6.43; N, 7.90.

[1752] Synthesis example G3:

[1753] The synthesis method was similar to that of G1, a yellow solid, with a yield of 70%. Mass spectrometry: m / z 927.35, elemental analysis experimental values: C, 81.53; H, 4.78; F, 6.14; N, 7.55.

[1754] Synthesis example G4:

[1755] The synthesis method was similar to that of G1, a yellow solid, with a yield of 72%. Mass spectrometry: m / z 969.40, elemental analysis experimental values: C, 81.71; H, 5.20; F, 5.87; N, 7.22.

[1756] Synthesis Example G5:

[1757] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 71%. Mass spectrum: m / z 1095.54. Experimental values of elemental analysis: C, 82.16; H, 6.25; F, 5.20; N, 6.39.

[1758] Synthesis Example G6:

[1759] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1011.45. Experimental values of elemental analysis: C, 81.87; H, 5.58; F, 5.63; N, 6.92.

[1760] Synthesis Example G7:

[1761] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1179.64. Experimental values of elemental analysis: C, 82.41; H, 6.83; F, 4.83; N, 5.93.

[1762] Synthesis Example G8:

[1763] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1059.38. Experimental values of elemental analysis: C, 74.75; H, 5.32; F, 5.37; N, 6.60; Si, 7.95

[1764] Synthesis Example G9:

[1765] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1261.48. Experimental values of elemental analysis: C, 70.37; H, 6.23; F, 4.51; N, 5.55; Si, 13.34.

[1766] Synthesis Example G10:

[1767] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 918.25. Experimental values of elemental analysis: C, 78.42; H, 3.18; F, 6.20; N, 12.19.

[1768] Synthesis Example G11:

[1769] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 993.23. Experimental values of elemental analysis: C, 76.13; H, 2.64; F, 5.73; N, 15.50.

[1770] Synthesis Example G12:

[1771] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 76%. Mass spectrometry: m / z 1071.35. Experimental values of elemental analysis: C, 84.02; H, 4.14; F, 5.32; N, 6.53.

[1772] Synthesis Example G13:

[1773] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 1299.45. Experimental values of elemental analysis: C, 85.89; H, 4.34; F, 4.38; N, 5.39.

[1774] Synthesis Example G14:

[1775] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1047.22. Experimental values of elemental analysis: C, 68.77; H, 2.79; F, 21.76; N, 6.68.

[1776] Synthesis Example G15:

[1777] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 1251.19. Experimental values of elemental analysis: C, 60.44; H, 2.09; F, 31.87; N, 5.59.

[1778] Synthesis Example G16:

[1779] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1197.50. Experimental values of elemental analysis: C, 84.19; H, 5.21; F, 4.76; N, 5.84.

[1780] Synthesis Example G17:

[1781] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1551.73. Experimental values of elemental analysis: C, 85.85; H, 5.97; F, 3.67; N, 4.51.

[1782] Synthesis Example G18:

[1783] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1784] Synthesis Example G19:

[1785] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1786] Synthesis Example G20:

[1787] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1788] Synthesis Example G21:

[1789] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 846.25. Experimental values of elemental analysis: C, 76.59; H, 3.45; F, 6.73; N, 13.23.

[1790] Synthesis Example G22:

[1791] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 81%. Mass spectrometry: m / z 891.25. Experimental values of elemental analysis: C, 76.76; H, 3.62; F, 6.39; N, 7.85; O, 5.38

[1792] Synthesis Example G23:

[1793] The synthesis method is similar to that of G1. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 939.18. Experimental values of elemental analysis: C, 72.83; H, 3.43; F, 6.06; N, 7.45; S, 10.23.

[1794] Synthesis Example G24:

[1795] Weigh intermediate 50 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq) and dissolve them in anhydrous DMF. Heat the mixture to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G24 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 929.25. Experimental values of elemental analysis: C, 73.62; H, 3.47; F, 18.39; N, 4.52.

[1796] Synthesis Example G25:

[1797] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 971.29. Experimental values of elemental analysis: C, 74.14; H, 3.94; F, 17.59; N, 4.32.

[1798] Synthesis Example G26:

[1799] The synthesis method is similar to that of G24, yellow solid, yield 71%. Mass spectrum: m / z 1013.34, experimental values of elemental analysis: C, 74.62; H, 4.37; F, 16.86; N, 4.14.

[1800] Synthesis Example G27:

[1801] The synthesis method is similar to that of G24, yellow solid, yield 73%. Mass spectrum: m / z 1055.39, experimental values of elemental analysis: C, 75.06; H, 4.77; F, 16.19; N, 3.98.

[1802] Synthesis Example G28:

[1803] The synthesis method is similar to that of G24, yellow solid, yield 69%. Mass spectrum: m / z 1181.53, experimental values of elemental analysis: C, 76.19; H, 5.80; F, 14.46; N, 3.55

[1804] Synthesis Example G29:

[1805] The synthesis method is similar to that of G24, yellow solid, yield 67%. Mass spectrum: m / z 1097.43, experimental values of elemental analysis: C, 75.46; H, 5.14; F, 15.57; N, 3.83

[1806] Synthesis Example G30:

[1807] The synthesis method is similar to that of G24, yellow solid, yield 66%. Mass spectrum: m / z 1265.62, experimental values of elemental analysis: C, 76.82; H, 6.37; F, 13.50; N, 3.32

[1808] Synthesis Example G31:

[1809] The synthesis method is similar to that of G24, yellow solid, yield 80%. Mass spectrum: m / z 1145.36, experimental values of elemental analysis: C, 69.15; H, 4.92; F, 14.91; N, 3.67; Si, 7.35

[1810] Synthesis Example G32:

[1811] The synthesis method is similar to that of G24, yellow solid, yield 73%. Mass spectrum: m / z 1347.47, experimental values of elemental analysis: C, 65.89; H, 5.83; F, 12.68; N, 3.12; Si, 12.49

[1812] Synthesis Example G33:

[1813] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 72%. Mass spectrometry: m / z 1004.23. Experimental values of elemental analysis: C, 71.71; H, 2.91; F, 17.01; N, 8.36

[1814] Synthesis Example G34:

[1815] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 71%. Mass spectrometry: m / z 1079.22. Experimental values of elemental analysis: C, 70.07; H, 2.43; F, 15.83; N, 11.67

[1816] Synthesis Example G35:

[1817] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 69%. Mass spectrometry: m / z 1157.34. Experimental values of elemental analysis: C, 77.78; H, 3.83; F, 14.76; N, 3.63

[1818] Synthesis Example G36:

[1819] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1385.43. Experimental values of elemental analysis: C, 80.57; H, 4.07; F, 12.33; N, 3.03

[1820] Synthesis Example G37:

[1821] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1133.21. Experimental values of elemental analysis: C, 63.56; H, 2.58; F, 30.16; N, 3.71

[1822] Synthesis Example G38:

[1823] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 67%. Mass spectrometry: m / z 1337.17. Experimental values of elemental analysis: C, 56.56; H, 1.96; F, 38.34; N, 3.14

[1824] Synthesis Example G39:

[1825] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 78%. Mass spectrometry: m / z 1283.48. Experimental values of elemental analysis: C, 78.55; H, 4.87; F, 13.31; N, 3.27

[1826] Synthesis Example G40:

[1827] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1637.71, Experimental values of elemental analysis: C, 81.35; H, 5.66; F, 10.43; N, 2.56

[1828] Synthesis Example G41:

[1829] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1830] Synthesis Example G42:

[1831] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 80%. Mass spectrometry: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1832] Synthesis Example G43:

[1833] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 82%. Mass spectrometry: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1834] Synthesis Example G44:

[1835] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 932.23, Experimental values of elemental analysis: C, 69.53; H, 3.13; F, 18.33; N, 9.01

[1836] Synthesis Example G45:

[1837] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 79%. Mass spectrometry: m / z 977.23, Experimental values of elemental analysis: C, 70.01; H, 3.30; F, 17.49; N, 4.30; O, 4.91

[1838] Synthesis Example G46:

[1839] The synthesis method is similar to that of G24. It is a yellow solid with a yield of 75%. Mass spectrometry: m / z 1025.16, Experimental values of elemental analysis: C, 66.72; H, 3.14; F, 16.66; N, 4.10; S, 9.37

[1840] Synthesis Example G47:

[1841] Weigh intermediate 51 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G47 by column chromatography, as a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60, elemental analysis experimental values: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[1842] Synthesis Example G52:

[1843] The synthesis method is similar to that of G47, as a yellow solid with a yield of 70%. Mass spectrum: m / z 1569.79, elemental analysis experimental values: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[1844] Synthesis Example G53:

[1845] The synthesis method is similar to that of G47, as a yellow solid with a yield of 74%. Mass spectrum: m / z 1737.97, elemental analysis experimental values: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[1846] Synthesis Example G54:

[1847] The synthesis method is similar to that of G47, as a yellow solid with a yield of 75%. Mass spectrum: m / z 1617.72, elemental analysis experimental values: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[1848] Synthesis Example G55:

[1849] The synthesis method is similar to that of G47, as a yellow solid with a yield of 73%. Mass spectrum: m / z 1833.83, elemental analysis experimental values: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[1850] Synthesis Example G58:

[1851] The synthesis method is similar to that of G47, as a yellow solid with a yield of 69%. Mass spectrum: m / z 1629.69, elemental analysis experimental values: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[1852] Synthesis Example G59:

[1853] The synthesis method is similar to that of G47. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1857.79. Experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[1854] Synthesis Example G60:

[1855] The synthesis method is similar to that of G47. It is a yellow solid with a yield of 78%. Mass spectrum: m / z 1605.56. Experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[1856] Synthesis Example G61:

[1857] The synthesis method is similar to that of G47. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1809.52. Experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[1858] Synthesis Example G70:

[1859] Weigh intermediate 52 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G70 by column chromatography. It is a yellow solid with a yield of 83%. Mass spectrum: m / z 1401.60. Experimental values of elemental analysis: C, 81.37; H, 5.46; B, 1.54; F, 4.06; N, 3.00; O, 4.56.

[1860] Synthesis Example G75:

[1861] The synthesis method is similar to that of G70. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1569.79. Experimental values of elemental analysis: C, 81.83; H, 6.42; B, 1.38; F, 3.63; N, 2.68; O, 4.07.

[1862] Synthesis Example G76

[1863] The synthesis method is similar to that of G70. It is a yellow solid with a yield of 70%. Mass spectrum: m / z 1737.97. Experimental values of elemental analysis: C, 82.19; H, 7.19; B, 1.24; F, 3.28; N, 2.42; O, 3.68.

[1864] Synthesis Example G77:

[1865] The synthesis method is similar to that of G70, a yellow solid with a yield of 68%. Mass spectrum: m / z 1617.72, experimental values of elemental analysis: C, 77.16; H, 6.23; B, 1.34; F, 3.52; N, 2.60; O, 3.95; Si, 5.20.

[1866] Synthesis Example G78:

[1867] The synthesis method is similar to that of G70, a yellow solid with a yield of 66%. Mass spectrum: m / z 1833.83, experimental values of elemental analysis: C, 73.95; H, 6.81; B, 1.18; F, 3.11; N, 2.29; O, 3.49; Si, 9.18

[1868] Synthesis Example G81:

[1869] The synthesis method is similar to that of G70, a yellow solid with a yield of 77%. Mass spectrum: m / z 1629.69, experimental values of elemental analysis: C, 83.24; H, 5.44; B, 1.33; F, 3.50; N, 2.58; O, 3.92.

[1870] Synthesis Example G82:

[1871] The synthesis method is similar to that of G70, a yellow solid with a yield of 77%. Mass spectrum: m / z 1857.79, experimental values of elemental analysis: C, 84.64; H, 5.42; B, 1.16; F, 3.07; N, 2.26; O, 3.44.

[1872] Synthesis Example G83:

[1873] The synthesis method is similar to that of G70, a yellow solid with a yield of 74%. Mass spectrum: m / z 1605.56, experimental values of elemental analysis: C, 73.28; H, 4.58; B, 1.35; F, 14.19; N, 2.62; O, 3.98.

[1874] Synthesis Example G84:

[1875] The synthesis method is similar to that of G70, a yellow solid with a yield of 71%. Mass spectrum: m / z 1809.52, experimental values of elemental analysis: C, 67.01; H, 3.90; B, 1.19; F, 22.04; N, 2.32; O, 3.54.

[1876] Synthesis Example G93:

[1877] Weigh intermediate 53 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G93 by column chromatography. It is a yellow solid with a yield of 85%. Mass spectrometry: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1878] Synthesis Example G94:

[1879] The synthesis method is similar to that of G93. It is a yellow solid with a yield of 71%. Mass spectrometry: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1880] Synthesis Example G95:

[1881] The synthesis method is similar to that of G93. It is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1882] Synthesis Example G96:

[1883] The synthesis method is similar to that of G93. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1884] Synthesis Example G97:

[1885] The synthesis method is similar to that of G93. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1886] Synthesis Example G98:

[1887] The synthesis method is similar to that of G93. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1888] Synthesis Example G99:

[1889] The synthesis method is similar to that of G93, yellow solid, yield 59%. Mass spectrometry: m / z 1365.66, experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1890] Synthesis Example G100:

[1891] The synthesis method is similar to that of G93, yellow solid, yield 61%. Mass spectrometry: m / z 1245.40, experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1892] Synthesis Example G101:

[1893] The synthesis method is similar to that of G93, yellow solid, yield 63%. Mass spectrometry: m / z 1461.52, experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1894] Synthesis Example G102:

[1895] The synthesis method is similar to that of G93, yellow solid, yield 73%. Mass spectrometry: m / z 1104.27, experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1896] Synthesis Example G103:

[1897] The synthesis method is similar to that of G93, yellow solid, yield 72%. Mass spectrometry: m / z 1179.25, experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1898] Synthesis Example G104:

[1899] The synthesis method is similar to that of G93, yellow solid, yield 79%. Mass spectrometry: m / z 1257.38, experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1900] Synthesis Example G105:

[1901] The synthesis method is similar to that of G93, yellow solid, yield 79%. Mass spectrometry: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1902] Synthesis Example G106:

[1903] The synthesis method is similar to G93. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1904] Synthesis Example G107:

[1905] The synthesis method is similar to G93. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1906] Synthesis Example G108:

[1907] The synthesis method is similar to G93. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1908] Synthesis Example G109:

[1909] The synthesis method is similar to G93. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1910] Synthesis Example G110:

[1911] The synthesis method is similar to G93. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1912] Synthesis Example G111:

[1913] The synthesis method is similar to G93. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1914] Synthesis Example G112:

[1915] The synthesis method is similar to G93. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1916] Synthesis Example G113:

[1917] The synthesis method is similar to that of G93, a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1918] Synthesis Example G114:

[1919] The synthesis method is similar to that of G93, a yellow solid with a yield of 74%. Mass spectrum: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1920] Synthesis Example G115:

[1921] The synthesis method is similar to that of G93, a yellow solid with a yield of 72%. Mass spectrum: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1922] Synthesis Example G116:

[1923] Weigh intermediate 54 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq) and dissolve them in anhydrous DMF. Heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G116 by column chromatography, a yellow solid with a yield of 83%. Mass spectrum: m / z 1029.28, experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1924] Synthesis Example G117:

[1925] The synthesis method is similar to that of G116, a yellow solid with a yield of 77%. Mass spectrum: m / z 1071.33, experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1926] Synthesis Example G118:

[1927] The synthesis method is similar to that of G116, a yellow solid with a yield of 70%. Mass spectrum: m / z 1113.38, experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1928] Synthesis Example G119:

[1929] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1930] Synthesis Example G120:

[1931] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 58%. Mass spectrum: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1932] Synthesis Example G121:

[1933] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1934] Synthesis Example G122:

[1935] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1936] Synthesis Example G123:

[1937] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1938] Synthesis Example G124:

[1939] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1940] Synthesis Example G125:

[1941] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1942] Synthesis Example G126:

[1943] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1944] Synthesis Example G127:

[1945] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1946] Synthesis Example G128:

[1947] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1948] Synthesis Example G129:

[1949] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1950] Synthesis Example G130:

[1951] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1952] Synthesis Example G131:

[1953] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[1954] Synthesis Example G132:

[1955] The synthesis method is similar to that of G116. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[1956] Synthesis Example G133:

[1957] The synthesis method is similar to that of G116, yellow solid, yield 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1958] Synthesis Example G134:

[1959] The synthesis method is similar to that of G116, yellow solid, yield 75%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1960] Synthesis Example G135:

[1961] The synthesis method is similar to that of G116, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1962] Synthesis Example G136:

[1963] The synthesis method is similar to that of G116, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[1964] Synthesis Example G137:

[1965] The synthesis method is similar to that of G116, yellow solid, yield 74%. Mass spectrometry: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[1966] Synthesis Example G138:

[1967] The synthesis method is similar to that of G116, yellow solid, yield 72%. Mass spectrometry: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[1968] Synthesis Example G139:

[1969] Weigh intermediate 55 (1 Eq), carbazole (4.4 Eq), and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G139 by column chromatography, which is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1029.28, elemental analysis experimental values: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[1970] Synthesis Example G140:

[1971] The synthesis method is similar to that of G139, which is a yellow solid with a yield of 77%. Mass spectrometry: m / z 1071.33, elemental analysis experimental values: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[1972] Synthesis Example G141:

[1973] The synthesis method is similar to that of G139, which is a yellow solid with a yield of 70%. Mass spectrometry: m / z 1113.38, elemental analysis experimental values: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[1974] Synthesis Example G142:

[1975] The synthesis method is similar to that of G139, which is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1155.42, elemental analysis experimental values: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[1976] Synthesis Example G143:

[1977] The synthesis method is similar to that of G139, which is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1281.56, elemental analysis experimental values: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[1978] Synthesis Example G144:

[1979] The synthesis method is similar to that of G139, which is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47, elemental analysis experimental values: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[1980] Synthesis Example G145:

[1981] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 59%. Mass spectrum: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[1982] Synthesis Example G146:

[1983] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 61%. Mass spectrum: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[1984] Synthesis Example G147:

[1985] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 63%. Mass spectrum: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[1986] Synthesis Example G148:

[1987] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 73%. Mass spectrum: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[1988] Synthesis Example G149:

[1989] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 72%. Mass spectrum: m / z 1179.25. Experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[1990] Synthesis Example G150:

[1991] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1257.38. Experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[1992] Synthesis Example G151:

[1993] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1485.47. Experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[1994] Synthesis Example G152:

[1995] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 74%. Mass spectrum: m / z 1233.24. Experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[1996] Synthesis Example G153:

[1997] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 69%. Mass spectrum: m / z 1437.21. Experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[1998] Synthesis Example G154:

[1999] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 55%. Mass spectrum: m / z 1383.52. Experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[2000] Synthesis Example G155:

[2001] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 80%. Mass spectrum: m / z 1737.75. Experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[2002] Synthesis Example G156:

[2003] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2004] Synthesis Example G157:

[2005] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 75%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2006] Synthesis Example G158:

[2007] The synthesis method is similar to that of G139. It is a yellow solid with a yield of 79%. Mass spectrum: m / z 1032.27. Experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2008] Synthesis Example G159:

[2009] The synthesis method is similar to that of G139, yellow solid, yield 79%. Mass spectrometry: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2010] Synthesis Example G160:

[2011] The synthesis method is similar to that of G139, yellow solid, yield 74%. Mass spectrometry: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[2012] Synthesis Example G161:

[2013] The synthesis method is similar to that of G139, yellow solid, yield 72%. Mass spectrometry: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[2014] Synthesis Example G162:

[2015] Weigh intermediate 56 (1 Eq), carbazole (4.4 Eq) and sodium hydride (6 Eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound G162 by column chromatography, yellow solid, yield 83%. Mass spectrometry: m / z 1029.28, experimental values of elemental analysis: C, 80.46; H, 3.72; F, 5.53; N, 4.08; O, 6.21.

[2016] Synthesis Example G163:

[2017] The synthesis method is similar to that of G162, yellow solid, yield 77%. Mass spectrometry: m / z 1071.33, experimental values of elemental analysis: C, 80.66; H, 4.14; F, 5.32; N, 3.92; O, 5.97.

[2018] Synthesis Example G164:

[2019] The synthesis method is similar to that of G162, yellow solid, yield 70%. Mass spectrometry: m / z 1113.38, experimental values of elemental analysis: C, 80.85; H, 4.52; F, 5.12; N, 3.77; O, 5.74.

[2020] Synthesis Example G165:

[2021] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1155.42. Experimental values of elemental analysis: C, 81.02; H, 4.88; F, 4.93; N, 3.63; O, 5.53.

[2022] Synthesis Example G166:

[2023] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 58%. Mass spectrometry: m / z 1281.56. Experimental values of elemental analysis: C, 81.47; H, 5.82; F, 4.44; N, 3.28; O, 4.99.

[2024] Synthesis Example G167:

[2025] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 55%. Mass spectrometry: m / z 1197.47. Experimental values of elemental analysis: C, 81.18; H, 5.21; F, 4.76; N, 3.51; O, 5.34.

[2026] Synthesis Example G168:

[2027] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 59%. Mass spectrometry: m / z 1365.66. Experimental values of elemental analysis: C, 81.73; H, 6.34; F, 4.17; N, 3.07; O, 4.68.

[2028] Synthesis Example G169:

[2029] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 61%. Mass spectrometry: m / z 1245.40. Experimental values of elemental analysis: C, 75.15; H, 5.01; F, 4.57; N, 3.37; O, 5.13; Si, 6.76.

[2030] Synthesis Example G170:

[2031] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1461.52. Experimental values of elemental analysis: C, 71.42; H, 5.92; F, 3.90; N, 2.87; O, 4.37; Si, 11.52.

[2032] Synthesis Example G171:

[2033] The synthesis method is similar to that of G162. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1104.27. Experimental values of elemental analysis: C, 78.25; H, 3.19; F, 5.16; N, 7.60; O, 5.79.

[2034] Synthesis Example G172:

[2035] The synthesis method is similar to that of G162, yellow solid, yield 72%. Mass spectrum: m / z 1179.25, experimental values of elemental analysis: C, 76.33; H, 2.73; F, 4.83; N, 10.68; O, 5.42.

[2036] Synthesis Example G173:

[2037] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1257.38, experimental values of elemental analysis: C, 83.04; H, 4.01; F, 4.53; N, 3.34; O, 5.09.

[2038] Synthesis Example G174:

[2039] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1485.47, experimental values of elemental analysis: C, 84.83; H, 4.20; F, 3.83; N, 2.83; O, 4.30.

[2040] Synthesis Example G175:

[2041] The synthesis method is similar to that of G162, yellow solid, yield 74%. Mass spectrum: m / z 1233.24, experimental values of elemental analysis: C, 70.08; H, 2.86; F, 18.47; N, 3.41; O, 5.19

[2042] Synthesis Example G176:

[2043] The synthesis method is similar to that of G162, yellow solid, yield 69%. Mass spectrum: m / z 1437.21, experimental values of elemental analysis: C, 62.64; H, 2.24; F, 27.74; N, 2.92; O, 4.45.

[2044] Synthesis Example G177:

[2045] The synthesis method is similar to that of G162, yellow solid, yield 55%. Mass spectrum: m / z 1383.52, experimental values of elemental analysis: C, 83.28; H, 4.95; F, 4.12; N, 3.03; O, 4.62.

[2046] Synthesis Example G178:

[2047] The synthesis method is similar to that of G162, yellow solid, yield 80%. Mass spectrum: m / z 1737.75, experimental values of elemental analysis: C, 84.95; H, 5.68; F, 3.28; N, 2.42; O, 3.68.

[2048] Synthesis Example G179:

[2049] The synthesis method is similar to that of G162, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2050] Synthesis Example G180:

[2051] The synthesis method is similar to that of G162, yellow solid, yield 75%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2052] Synthesis Example G181:

[2053] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2054] Synthesis Example G182:

[2055] The synthesis method is similar to that of G162, yellow solid, yield 79%. Mass spectrum: m / z 1032.27, experimental values of elemental analysis: C, 76.74; H, 3.42; F, 5.52; N, 8.14; O, 6.19.

[2056] Synthesis Example G183:

[2057] The synthesis method is similar to that of G162, yellow solid, yield 74%. Mass spectrum: m / z 1077.27, experimental values of elemental analysis: C, 76.87; H, 3.55; F, 5.29; N, 3.90; O, 10.39.

[2058] Synthesis Example G184:

[2059] The synthesis method is similar to that of G162, yellow solid, yield 72%. Mass spectrum: m / z 1125.20, experimental values of elemental analysis: C, 73.59; H, 3.40; F, 5.06; N, 3.73; O, 5.68; S, 8.54.

[2060] Synthesis of Intermediate 57:

[2061]

[2062] 1-Bromo-2,3,4,6-tetrafluoro-5-(trifluoromethyl)benzene (10 g, 33.67 mmol), (2,12-bis(trifluoromethyl))-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracen-7-yl)boronic acid (16.66 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.61 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain the white solid intermediate 57, weighing 15.0 g, with a yield of 72%.

[2063] Synthesis of intermediates 58 - 63:

[2064]

[2065] The synthesis method was similar to that of intermediate 57. Intermediates 58 - 63 were all white solids, with yields of 59%, 66%, 68%, 59%, 63%, and 66% respectively. Synthesis Example H1:

[2066] Intermediate 57 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was filtered, collected, dried, and purified by column chromatography to obtain compound H1, a yellow solid, with a yield of 52%. Mass spectrometry: m / z 1210.31, elemental analysis experimental values: C, 74.39; H, 3.33; B, 0.89; F, 14.12; N, 4.63; O, 2.64.

[2067] Synthesis Example H2:

[2068] The synthesis method was similar to that of H1, a yellow solid, with a yield of 55%. Mass spectrometry: m / z 1434.56, elemental analysis experimental values: C, 76.15; H, 5.06; B, 0.75; F, 11.91; N, 3.90; O, 2.23.

[2069] Synthesis Example H3:

[2070] The synthesis method was similar to that of H1, a yellow solid, with a yield of 53%. Mass spectrometry: m / z 1658.81, elemental analysis experimental values: C, 77.43; H, 6.32; B, 0.65; F, 10.30; N, 3.38; O, 1.93.

[2071] Synthesis Example H4:

[2072] The synthesis method is similar to that of H1. It is a yellow solid with a yield of 57%. Mass spectrometry: m / z 1514.44. Experimental values of elemental analysis: C, 78.47; H, 3.73; B, 0.71; F, 11.28; N, 3.70; O, 2.11.

[2073] Synthesis Example H5:

[2074] The synthesis method is similar to that of H1. It is a yellow solid with a yield of 47%. Mass spectrometry: m / z 1818.56. Experimental values of elemental analysis: C, 81.18; H, 3.99; B, 0.59; F, 9.40; N, 3.08; O, 1.76.

[2075] Synthesis Example H6:

[2076] Weigh intermediate 58 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound H6 by column chromatography. It is a yellow solid with a yield of 68%. Mass spectrometry: m / z 1210.31. Experimental values of elemental analysis: C, 74.39; H, 3.33; B, 0.89; F, 14.12; N, 4.63; O, 2.64.

[2077] Synthesis Example H7:

[2078] The synthesis method is similar to that of H6. It is a yellow solid with a yield of 64%. Mass spectrometry: m / z 1434.56. Experimental values of elemental analysis: C, 76.15; H, 5.06; B, 0.75; F, 11.91; N, 3.90; O, 2.23.

[2079] Synthesis Example H8:

[2080] The synthesis method is similar to that of H6. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1658.81. Experimental values of elemental analysis: C, 77.43; H, 6.32; B, 0.65; F, 10.30; N, 3.38; O, 1.93.

[2081] Synthesis Example H9:

[2082] The synthesis method is similar to that of H6. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1514.44. Experimental values of elemental analysis: C, 78.47; H, 3.73; B, 0.71; F, 11.28; N, 3.70; O, 2.11.

[2083] Synthesis Example H10:

[2084] The synthesis method is similar to that of H6. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1818.56. Experimental values of elemental analysis: C, 81.18; H, 3.99; B, 0.59; F, 9.40; N, 3.08; O, 1.76.

[2085] Synthesis Example H11:

[2086] Weigh intermediate 59 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound H11 by column chromatography. It is a yellow solid with a yield of 66%. Mass spectrometry: m / z 1449.30. Experimental values of elemental analysis: C, 68.76; H, 2.78; B, 1.49; F, 19.66; N, 2.90; O, 4.41.

[2087] Synthesis Example H12:

[2088] The synthesis method is similar to that of H11. It is a yellow solid with a yield of 62%. Mass spectrometry: m / z 1617.48. Experimental values of elemental analysis: C, 70.51; H, 3.99; B, 1.34; F, 17.61; N, 2.60; O, 3.95.

[2089] Synthesis Example H13:

[2090] The synthesis method is similar to that of H11. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1785.67. Experimental values of elemental analysis: C, 71.94; H, 4.97; B, 1.21; F, 15.95; N, 2.35; O, 3.58.

[2091] Synthesis Example H14:

[2092] The synthesis method is similar to that of H11. It is a yellow solid with a yield of 74%. Mass spectrometry: m / z 1677.39. Experimental values of elemental analysis: C, 72.29; H, 3.12; B, 1.29; F, 16.98; N, 2.50; O, 3.81.

[2093] Synthesis Example H15:

[2094] The synthesis method is similar to that of H11. It is a yellow solid with a yield of 63%. Mass spectrometry: m / z 1905.48. Experimental values of elemental analysis: C, 74.97; H, 3.38; B, 1.13; F, 14.95; N, 2.20; O, 3.36.

[2095] Synthesis Example H16:

[2096] Weigh intermediate 60 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound H16 by column chromatography, which is a yellow solid with a yield of 62%. Mass spectrum: m / z 1449.30, elemental analysis experimental values: C, 68.76; H, 2.78; B, 1.49; F, 19.66; N, 2.90; O, 4.41.

[2097] Synthesis Example H17:

[2098] The synthesis method is similar to that of H16, which is a yellow solid with a yield of 52%. Mass spectrum: m / z 1617.48, elemental analysis experimental values: C, 70.51; H, 3.99; B, 1.34; F, 17.61; N, 2.60; O, 3.95.

[2099] Synthesis Example H18:

[2100] The synthesis method is similar to that of H16, which is a yellow solid with a yield of 76%. Mass spectrum: m / z 1785.67, elemental analysis experimental values: C, 71.94; H, 4.97; B, 1.21; F, 15.95; N, 2.35; O, 3.58.

[2101] Synthesis Example H19:

[2102] The synthesis method is similar to that of H16, which is a yellow solid with a yield of 72%. Mass spectrum: m / z 1677.39, elemental analysis experimental values: C, 72.29; H, 3.12; B, 1.29; F, 16.98; N, 2.50; O, 3.81.

[2103] Synthesis Example H20:

[2104] The synthesis method is similar to that of H16, which is a yellow solid with a yield of 73%. Mass spectrum: m / z 1905.48, elemental analysis experimental values: C, 74.97; H, 3.38; B, 1.13; F, 14.95; N, 2.20; O, 3.36.

[2105] Synthesis Example H21:

[2106] Intermediate 61 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain Compound H21, a yellow solid, with a yield of 68%. Mass spectrometry: m / z 1449.30, elemental analysis experimental values: C, 68.76; H, 2.78; B, 1.49; F, 19.66; N, 2.90; O, 4.41.

[2107] Synthesis Example H22:

[2108] The synthesis method was similar to that of H21, a yellow solid, with a yield of 59%. Mass spectrometry: m / z 1617.48, elemental analysis experimental values: C, 70.51; H, 3.99; B, 1.34; F, 17.61; N, 2.60; O, 3.95.

[2109] Synthesis Example H23:

[2110] The synthesis method was similar to that of H21, a yellow solid, with a yield of 66%. Mass spectrometry: m / z 1785.67, elemental analysis experimental values: C, 71.94; H, 4.97; B, 1.21; F, 15.95; N, 2.35; O, 3.58.

[2111] Synthesis Example H24:

[2112] The synthesis method was similar to that of H21, a yellow solid, with a yield of 63%. Mass spectrometry: m / z 1677.39, elemental analysis experimental values: C, 72.29; H, 3.12; B, 1.29; F, 16.98; N, 2.50; O, 3.81.

[2113] Synthesis Example H25:

[2114] The synthesis method was similar to that of H21, a yellow solid, with a yield of 74%. Mass spectrometry: m / z 1905.48, elemental analysis experimental values: C, 74.97; H, 3.38; B, 1.13; F, 14.95; N, 2.20; O, 3.36.

[2115] Synthesis Example H26:

[2116] Intermediate 62 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound H16 as a yellow solid with a yield of 64%. Mass spectrum: m / z 1449.30, elemental analysis experimental values: C, 68.76; H, 2.78; B, 1.49; F, 19.66; N, 2.90; O, 4.41.

[2117] Synthesis Example H27:

[2118] The synthesis method was similar to that of H26, obtaining a yellow solid with a yield of 63%. Mass spectrum: m / z 1617.48, elemental analysis experimental values: C, 70.51; H, 3.99; B, 1.34; F, 17.61; N, 2.60; O, 3.95.

[2119] Synthesis Example H28:

[2120] The synthesis method was similar to that of H26, obtaining a yellow solid with a yield of 84%. Mass spectrum: m / z 1785.67, elemental analysis experimental values: C, 71.94; H, 4.97; B, 1.21; F, 15.95; N, 2.35; O, 3.58.

[2121] Synthesis Example H29:

[2122] The synthesis method was similar to that of H26, obtaining a yellow solid with a yield of 63%. Mass spectrum: m / z 1677.39, elemental analysis experimental values: C, 72.29; H, 3.12; B, 1.29; F, 16.98; N, 2.50; O, 3.81.

[2123] Synthesis Example H30:

[2124] The synthesis method was similar to that of H26, obtaining a yellow solid with a yield of 64%. Mass spectrum: m / z 1905.48, elemental analysis experimental values: C, 74.97; H, 3.38; B, 1.13; F, 14.95; N, 2.20; O, 3.36.

[2125] Synthesis Example H31:

[2126] Intermediate 63 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) were weighed and dissolved in anhydrous DMF. The mixture was heated to 80 °C and stirred for 12 h. After cooling, the reaction system was poured into cold water, and the pH was adjusted to neutral with dilute hydrochloric acid. The precipitate was collected by filtration, dried, and purified by column chromatography to obtain compound H31, a yellow solid, with a yield of 69%. Mass spectrometry: m / z 1449.30, elemental analysis experimental values: C, 68.76; H, 2.78; B, 1.49; F, 19.66; N, 2.90; O, 4.41.

[2127] Synthesis Example H32:

[2128] The synthesis method was similar to that of H31, a yellow solid, with a yield of 64%. Mass spectrometry: m / z 1617.48, elemental analysis experimental values: C, 70.51; H, 3.99; B, 1.34; F, 17.61; N, 2.60; O, 3.95.

[2129] Synthesis Example H33:

[2130] The synthesis method was similar to that of H31, a yellow solid, with a yield of 79%. Mass spectrometry: m / z 1785.67, elemental analysis experimental values: C, 71.94; H, 4.97; B, 1.21; F, 15.95; N, 2.35; O, 3.58.

[2131] Synthesis Example H34:

[2132] The synthesis method was similar to that of H31, a yellow solid, with a yield of 75%. Mass spectrometry: m / z 1677.39, elemental analysis experimental values: C, 72.29; H, 3.12; B, 1.29; F, 16.98; N, 2.50; O, 3.81.

[2133] Synthesis Example H35:

[2134] The synthesis method was similar to that of H31, a yellow solid, with a yield of 73%. Mass spectrometry: m / z 1905.48, elemental analysis experimental values: C, 74.97; H, 3.38; B, 1.13; F, 14.95; N, 2.20; O, 3.36.

[2135] Synthesis of Intermediate 64:

[2136]

[2137] 1-Bromo-2,3,4,6-tetrafluoro-5-(trifluoromethyl)benzene (10 g, 33.67 mmol), (3,11-bis(trifluoromethyl))-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracen-7-yl)boronic acid (16.66 g, 37.04 mmol) were dissolved in 150 mL of toluene. Tetrakis(triphenylphosphine)palladium (1.95 g, 1.68 mmol) and 20 mL of aqueous potassium carbonate solution (9.61 g, 67.35 mmol) were added. The mixture was heated under reflux for 24 h. After cooling, the layers were separated, extracted, dried, and purified by column chromatography (petroleum ether:dichloromethane = 3:1) to obtain 15.0 g of white solid intermediate 64 with a yield of 57%.

[2138] Synthesis of intermediates 65 - 70:

[2139]

[2140] The synthesis method was similar to that of intermediate 64. Intermediates 65 - 70 were all white solids with yields of 74%, 67%, 68%, 72%, 64%, and 66% respectively.

[2141] Synthesis example I1:

[2142] Weigh intermediate 64 (1 eq), carbazole (4.4 eq), and sodium hydride (6 eq) and dissolve them in anhydrous DMF. Heat the mixture to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and purify by column chromatography to obtain compound I1 as a yellow solid with a yield of 74%. Mass spectrometry: m / z 1210.31, elemental analysis experimental values: C, 74.39; H, 3.33; B, 0.89; F, 14.12; N, 4.63; O, 2.64.

[2143] Synthesis example I2:

[2144] The synthesis method was similar to that of I1, and it was a yellow solid with a yield of 64%. Mass spectrometry: m / z 1434.56, elemental analysis experimental values: C, 76.15; H, 5.06; B, 0.75; F, 11.91; N, 3.90; O, 2.23.

[2145] Synthesis example I3:

[2146] The synthesis method was similar to that of I1, and it was a yellow solid with a yield of 64%. Mass spectrometry: m / z 1658.81, elemental analysis experimental values: C, 77.43; H, 6.32; B, 0.65; F, 10.30; N, 3.38; O, 1.93.

[2147] Synthesis example I4:

[2148] The synthesis method is similar to that of I1. It is a yellow solid with a yield of 84%. Mass spectrometry: m / z 1514.44. Experimental values of elemental analysis: C, 78.47; H, 3.73; B, 0.71; F, 11.28; N, 3.70; O, 2.11.

[2149] Synthesis Example I5:

[2150] The synthesis method is similar to that of I1. It is a yellow solid with a yield of 45%. Mass spectrometry: m / z 1818.56. Experimental values of elemental analysis: C, 81.18; H, 3.99; B, 0.59; F, 9.40; N, 3.08; O, 1.76.

[2151] Synthesis Example I6:

[2152] Weigh intermediate 65 (1 eq), carbazole (4.4 eq) and sodium hydride (6 eq), dissolve them in anhydrous DMF, heat to 80 °C and stir for 12 h. After cooling, pour the reaction system into cold water, adjust the pH to neutral with dilute hydrochloric acid, filter to collect the precipitate, dry it, and obtain compound I6 by column chromatography. It is a yellow solid with a yield of 47%. Mass spectrometry: m / z 1210.31. Experimental values of elemental analysis: C, 74.39; H, 3.33; B, 0.89; F, 14.12; N, 4.63; O, 2.64.

[2153] Synthesis Example I7:

[2154] The synthesis method is similar to that of I6. It is a yellow solid with a yield of 67%. Mass spectrometry: m / z 1434.56. Experimental values of elemental analysis: C, 76.15; H, 5.06; B, 0.75; F, 11.91; N, 3.90; O, 2.23.

[2155] Synthesis Example I8:

[2156] The synthesis method is similar to that of I6. It is a yellow solid with a yield of 73%. Mass spectrometry: m / z 1658.81. Experimental values of elemental analysis: C, 77.43; H, 6.32; B, 0.65; F, 10.30; N, 3.38; O, 1.93.

[2157] Synthesis Example I9:

[2158] The synthesis method is similar to that of I6. It is a yellow solid with a yield of 83%. Mass spectrometry: m / z 1514.44. Experimental values of elemental analysis: C, 78.47; H, 3.73; B, 0.71; F, 11.28; N, 3.70; O, 2.11.

[2159] Synthesis Example I10:

[2160] The synthesis method is similar to that o...

Claims

1. An organic compound having a structure represented by the following formula (1): In formula (1), D 1 , D 2 , D 3 , D 4 , D 5 are the same or different, and D 1 , D 2 , D 3 , D 4 , D 5 are each independently selected from the structures represented by the following formula (d2), formula (d3), formula (d4) or formula (d5), or are selected from substituted or unsubstituted C3-C60 heteroaryl; And D 1 , D 2 , D 3 , D 4 , D 5 at least one of which is selected from the structures represented by the following formula (d2)-(d5), and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl. When there are substituents on the heteroaryl, the substituents are selected from one or a combination of two of cyano, halogen, C1-C30 linear alkyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C2-C30 alkynyl, nitro, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 aryl, and C3-C60 heteroaryl; 2. The organic compound according to claim 1, wherein The said D 1 , D 2 , D 3 , D 4 , D 5 has one structure selected from the structures shown in one of formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 among them are four respectively and independently selected from substituted or unsubstituted C3-C60 heteroaryl groups; Alternatively, two of the D 1 , D 2 , D 3 , D 4 , D 5 are independently selected from the structures represented by one of formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time, three of the D 1 , D 2 , D 3 , D 4 , D 5 are independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

3. The organic compound according to claim 1, characterized in that, The said D 2 or D 3 is selected from the structures shown by one of formula (d2), formula (d3), formula (d4) or formula (d5), and at the same time D 1 , D 2 , D 3 , D 4 , D 5 Among them, the other four are each independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

4. The organic compound according to claim 1, characterized in that, The said D 3 is selected from the structures shown by one of formula (d2), formula (d3), formula (d4) or formula (d5), and meanwhile D 1 , D 2 , D 4 , D 5 are each independently selected from substituted or unsubstituted C3-C60 heteroaryl groups.

5. The organic compound according to any one of claims 1-4, characterized in that, When D 1 , D 2 , D 3 , D 4 , D 5 are each independently selected from substituted or unsubstituted C3-C60 heteroaryl, it is selected from one of the following substituted or unsubstituted structural formulas: When there are substituents on the above structural formula, the substituents are selected from one or a combination of two of deuterium, cyano group, halogen, C1-C6 linear alkyl group, C3-C6 cycloalkyl group, C1-C6 alkoxy group, C1-C6 thioalkoxy group, C6-C30 aryl group and C3-C60 heteroaryl group.

6. The organic compound according to any one of claims 1-4, characterized in that, When D 1 , D 2 , D 3 , D 4 , D 5 are each independently selected from substituted or unsubstituted C3-C60 heteroaryl, it is selected from one of the following substituted or unsubstituted structural formulas: When there are substituents on the above structural formula, the substituents are selected from one of deuterium, C1-C6 linear alkyl group, C3-C6 cycloalkyl group, C6-C30 aryl group and C3-C30 heteroaryl group.

7. An organic compound selected from the following structures:

8. Use of the compound according to any one of claims 1-7 as a functional material in an organic electronic device, the organic electronic device including an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper.

9. The use of the compound according to claim 8 is as a light-emitting layer material in an organic electroluminescent device, specifically as a light-emitting dye in the light-emitting layer.

10. An organic electroluminescent device including a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1-7; The described light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is located between the hole transport region and the electron transport region; among them, The light-emitting layer contains the compound according to any one of claims 1-7.

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